Synthetic Studies toward the Total Synthesis of Amphidinolide H1

Lisheng Deng; Zhixiong Ma; Gang Zhao

doi:10.1055/s-2008-1032101

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2008(5): 728-732
DOI: 10.1055/s-2008-1032101

LETTER

Synthetic Studies toward the Total Synthesis of Amphidinolide H1

Lisheng Deng, Zhixiong Ma, Gang Zhao*
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaog@mail.sioc.ac.cn;

Further Information

Publication History

Received 30 November 2007
Publication Date:
26 February 2008 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A convergent synthesis of the macrolide core as the immediate precursor to amphidinolide H1 is described, which features a palladium-catalyzed Stille cross-coupling, a methyl ketone diastereoselective aldol reaction, a Mitsunobu esterification, and an intramolecular ring-closing metathesis (RCM) reaction to construct the 26-membered macrocycle as key steps.

Key words

amphidinolide H1 - macrolide - aldol reaction - RCM reaction - Mitsunobu reaction

References and Notes

1 Kobayashi J. Ishibashi M. Nakamura H. Ohizumi Y. Tetrahedron Lett. 1986, 27: 5755

Crossref Google Scholar
Reviews:
2a Ishibashi M. Kobayashi J. Heterocycles 1997, 44: 543

Crossref PubMed Google Scholar
2b Kobayashi J. Ishibashi M. In Comprehensive Natural Products Chemistry Vol. 8: Mori K. Elsevier; New York: 1999. p.619-649

Crossref PubMed Google Scholar
2c Chakraborty TK. Das S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1: 131

Crossref PubMed Google Scholar
2d Kobayashi J. Tsuda M. Nat. Prod. Rep. 2004, 21: 77

Crossref PubMed Google Scholar
2e Kobayashi J. Kubota T. J. Nat. Prod. 2007, 70: 451

Crossref PubMed Google Scholar
For total syntheses of amphidinolides families, see:
3a Williams DR. Kissel WS. J. Am. Chem. Soc. 1998, 120: 11198

Google Scholar
3b Williams DR. Myers BJ. Mi L. Org. Lett. 2000, 2: 945

Google Scholar
3c Williams DR. Meyer KG. J. Am. Chem. Soc. 2001, 123: 765

Google Scholar
3d Lam HW. Pattenden G. Angew. Chem. Int. Ed. 2002, 41: 508

Google Scholar
3e Maleczka RE. Terrell LR. Geng F. Ward JS. Org. Lett. 2002, 4: 2841

Google Scholar
3f Trost BM. Chisholm JD. Wrobleski ST. Jung M. J. Am. Chem. Soc. 2002, 124: 12420

Google Scholar
3g Fürstner A. Aïssa C. Riveiros R. Ragot J. Angew. Chem. Int. Ed. 2002, 41: 4763

Google Scholar
3h Ghosh AK. Liu C. J. Am. Chem. Soc. 2003, 125: 2374

Google Scholar
3i Aïssa C. Riveiros R. Ragot J. Fürstner A. J. Am. Chem. Soc. 2003, 125: 15512

Google Scholar
3j Lepage O. Kattnig E. Fürstner A. J. Am. Chem. Soc. 2004, 126: 15970

Google Scholar
3k Ghosh AK. Gong G. J. Am. Chem. Soc. 2004, 126: 3704

Google Scholar
3l Trost BM. Harrington PE. J. Am. Chem. Soc. 2004, 126: 5028

Google Scholar
3m Trost BM. Papillon JPN. J. Am. Chem. Soc. 2004, 126: 13618

Google Scholar
3n Colby EA. O’Brien KC. Jamison TF. J. Am. Chem. Soc. 2004, 126: 998

Google Scholar
3o Colby EA. O’Brien KC. Jamison TF. J. Am. Chem. Soc. 2005, 127: 4297

Google Scholar
3p Trost BM. Harrington PE. Chisholm JD. Wrobleski ST. J. Am. Chem. Soc. 2005, 127: 13589

Google Scholar
3q Trost BM. Harrington PE. Chisholm JD. Wrobleski ST. J. Am. Chem. Soc. 2005, 127: 13598

Google Scholar
3r Trost BM. Papillon JPN. Nussbaumer T. J. Am. Chem. Soc. 2005, 127: 17921

Google Scholar
3s Fürstner A. Kattnig E. Lepage O. J. Am. Chem. Soc. 2006, 128: 9194

Google Scholar
3t Fürstner A. Larionov O. Flügge S. Angew. Chem. Int. Ed. 2007, 46: 5545

Google Scholar
3u Va P. Roush WR. J. Am. Chem. Soc. 2006, 128: 15960

Google Scholar
3v Kim CH. An HJ. Shin WK. Yu W. Woo SK. Jung SK. Lee E. Angew. Chem. Int. Ed. 2006, 45: 8019

Google Scholar
3w Nicolaou KC. Brenzovich WE. Bulger PG. Francis TM. Org. Biomol. Chem. 2006, 4: 2119

Google Scholar
3x Nicolaou KC. Bulger PG. Brenzovich WE. Org. Biomol. Chem. 2006, 4: 2158

Google Scholar
3y Jin J. Chen Y. Li Y. Wu J. Dai WM. Org. Lett. 2007, 9: 2585

Google Scholar
3z Colby EA. Jamison TF. Org. Biomol. Chem. 2005, 3: 2675

Google Scholar
4a Deng LS. Huang XP. Zhao G. J. Org. Chem. 2006, 71: 4625

Crossref PubMed Google Scholar
4b Fürstner A. Bouchez LC. Funel J.-A. Liepins V. Porée F.-H. Gilmour R. Beaufils F. Laurich D. Tamiya M. Angew. Chem. Int. Ed. 2007, 46: 9265

Crossref PubMed Google Scholar
5a Kobayashi J. Shigemori H. Ishibashi M. Yamasu T. Hirota H. Sasaki T. J. Org. Chem. 1991, 56: 5221

Google Scholar
5b Kobayashi J. Shimbo K. Sato M. Shiro M. Tsuda M. Org. Lett. 2000, 2: 2805

Google Scholar
6 Kobayashi J. Shimbo K. Sato M. Tsuda M. J. Org. Chem. 2002, 67: 6585

Crossref Google Scholar
Amphidinolide H and G:
7a Chakraborty TK. Suresh VR. Tetrahedron Lett. 1998, 39: 7775

Article in Thieme Connect Google Scholar
7b Chakraborty TK. Suresh VR. Tetrahedron Lett. 1998, 39: 9109

Article in Thieme Connect Google Scholar
7c Sato M. Shimbo K. Tsuda M. Kobayashi J. Tetrahedron Lett. 2000, 41: 503

Article in Thieme Connect Google Scholar
7d Liesener FP. Kalesse M. Synlett 2005, 2236

Article in Thieme Connect Google Scholar
7e Liesener FP. Jannsen U. Kalesse M. Synthesis 2006, 2590

Article in Thieme Connect Google Scholar
7f Petri AF. Schneekloth JS. Mandal AK. Crews CM. Org. Lett. 2007, 9: 3001

Article in Thieme Connect Google Scholar
7g Deng LS. Ma ZX. Zhang YZ. Zhao G. Synlett 2007, 87

Article in Thieme Connect Google Scholar
Structurally related amphidinolides B:
8a Gopalarathnam A. Nelson SG. Org. Lett. 2006, 8: 7

Crossref Google Scholar
8b Mandal AK. Schneekloth JS. Kuramochi K. Crews CM. Org. Lett. 2006, 8: 427

Crossref Google Scholar
8c Mandal AK. Schneekloth JS. Kuramochi K. Crews CM. Org. Lett. 2005, 7: 3645

Crossref Google Scholar
8d Zhang W. Carter RG. Org. Lett. 2005, 7: 4209

Crossref Google Scholar
8e Zhang W. Carter RG. Yokochi AFT. J. Org. Chem. 2004, 69: 2569

Crossref Google Scholar
8f Mandal AK. Schneekloth JS. Crews CM. Org. Lett. 2004, 6: 3645

Crossref Google Scholar
8g Cid MB. Pattenden G. Tetrahedron Lett. 2000, 41: 7373

Crossref Google Scholar
8h Lee D.-H. Rho M.-D. Tetrahedron Lett. 2000, 41: 2573

Crossref Google Scholar
8i Chakraborty TK. Thippeswamy D. Synlett 1999, 150

Crossref Google Scholar
8j Eng HM. Myles DC. Tetrahedron Lett. 1999, 40: 2279

Crossref Google Scholar
8k Ishiyama H. Takemura T. Tsuda M. Kobayashi J. J. Chem. Soc., Perkin Trans. 1 1999, 1163

Crossref Google Scholar
8l Ishiyama H. Takemura T. Tsuda M. Kobayashi J. Tetrahedron 1999, 55: 4583

Crossref Google Scholar
8m Ohi K. Nishiyama S. Synlett 1999, 573

Crossref Google Scholar
8n Ohi K. Nishiyama S. Synlett 1999, 571

Crossref Google Scholar
8o Cid MB. Pattenden G. Synlett 1998, 540

Crossref Google Scholar
8p Ohi K. Shima K. Hamada K. Saito Y. Yamada N. Ohba S. Nishiyama S. Bull. Chem. Soc. Jpn. 1998, 71: 2433

Crossref Google Scholar
8q Chakraborty TK. Thippeswamy D. Suresh VR. Jayaprakash S. Chem. Lett. 1997, 563

Crossref Google Scholar
8r Chakraborty TK. Suresh VR. Chem. Lett. 1997, 565

Crossref Google Scholar
8s Lee D.-H. Lee S.-W. Tetrahedron Lett. 1997, 38: 7909

Crossref Google Scholar
9 White JD. Kawasaki M. J. Org. Chem. 1992, 57: 5292

Crossref Google Scholar
10a Dess DB. Martin JC. J. Org. Chem. 1983, 48: 4155

Crossref Google Scholar
10b Corey EJ. Fuchs PL. Tetrahedron Lett. 1972, 13: 3769

Crossref Google Scholar
11a Yoshida Y. Negishi E. J. Am. Chem. Soc. 1981, 103: 4985

Google Scholar
11b Wipf P. Lim S. Angew. Chem., Int. Ed. Engl. 1993, 32: 1095

Google Scholar
12 Evans DA. Kim AS. Metternich R. Novack VJ. J. Am. Chem. Soc. 1998, 120: 5921

Crossref Google Scholar
13 Gao Y. Klunder JM. Hanson RM. Masamune H. Ko SY. Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765

Crossref Google Scholar
14a Milstein D. Stille JK. J. Am. Chem. Soc. 1978, 100: 3636

Google Scholar
14b Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

Google Scholar
15 Domínguez B. Iglesias B. de Lera AR. Tetrahedron 1999, 55: 15071

Crossref Google Scholar
17a Mitsunobu O. Yamada M. Bull. Chem. Soc. Jpn. 1967, 40: 2380

Article in Thieme Connect Google Scholar
17b Mitsunobu O. Synthesis 1981, 1

Article in Thieme Connect Google Scholar
18 Niwa H. Miyachi Y. Okamoto O. Uosaki Y. Kuroda A. Ishiwata H. Yamada K. Tetrahedron 1992, 48: 393

Crossref Google Scholar
20a Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

Google Scholar
20b Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490

Google Scholar
22 Giudicelli MB. Pieq D. Veyron B. Tetrahedron Lett. 1990, 31: 6527

Google Scholar

16

Aldehyde 4: [α]_D ²⁴ -4.0 (c 0.60, CHCl₃). IR (film): 2958, 2925, 1726, 1459, 1378, 1026 cm^-1. ¹H NMR (300 MHz, CDCl₃): δ = 5.60-5.40 (m, 3 H), 5.27-5.24 (m, 1 H), 4.96 (s, 1 H), 4.81 (s, 1 H), 3.51 (t, J = 7.5 Hz, 2 H), 3.05 (dd, J = 1.8, 6.9 Hz, 1 H), 2.84-2.80 (m, 1 H), 2.32-2.25 (m, 1 H), 2.12 (dd, J = 6.6, 6.9 Hz, 1 H), 1.94 (dd, J = 5.1, 7.8 Hz, 1 H), 1.97-2.04 (m, 1 H), 1.91 (s, 3 H), 1.90-1.40 (m, 4 H), 1.02 (d, J = 6.6 Hz, 3 H), 0.91 (d, J = 6.6 Hz, 3 H), 0.89 (s, 9 H), -0.33 (s, 6 H). ¹³C NMR (75 MHz, CDCl₃): δ = 202.4, 143.9, 140.8, 135.8, 125.9, 119.0, 115.1, 59.3, 59.2, 48.9, 45.8, 38.9, 37.8, 29.6, 19.6, 19.5, 15.0. MS (EI): m/z calcd for C₁₇H₂₆O₂ [M]⁺: 262; found: 262. HRMS (EI): m/z calcd for C₁₇H₂₆O₂ ⁺ [M]⁺: 262.1933; found: 262.1925.

19

The stereochemistry of at C18 was confirmed on basis of Mosher ester analysis.

21

Diol 2: [α]_D ²⁴ -2.2 (c 0.51, CHCl₃). IR (neat): 3488, 2925, 1708, 1456, 1263, 1151, 1028 cm^-1. ¹H NMR (500 Hz, CDCl₃): δ = 6.76 (t, J = 6.9 Hz, 1 H), 5.87 (dt, J = 6.8, 15.3 Hz, 1 H), 5.56 (s, 1 H), 5.23 (dd, J = 6.9, 14.6 Hz, 1 H), 5.04 (ddd, J = 3.2, 6.0, 12.6 Hz, 1 H), 4.97 (s, 1 H), 4.81 (s, 1 H), 4.74-4.60 (m, 4 H), 4.19 (d, J = 5.2 Hz, 1 H), 4.05-3.96 (m, 1 H), 3.76 (m, 1 H), 3.70 (m, 1 H), 3.65 (m, 1 H), 3.35 (s, 6 H), 3.09 (br s, 1 H), 3.02 (dd, J = 2.1, 7.9 Hz, 1 H), 2.85 (dt, J = 2.1, 8.6 Hz, 1 H), 2.76-2.63 (m, 2 H), 2.33-2.22 (m, 5 H), 2.16 (m, 1 H), 2.10 (dd, J = 5.1, 7.8 Hz, 1 H), 1.97-1.91 (m, 2 H), 1.83 (s, 3 H), 1.82 (m, 1 H), 1.74 (s, 3 H), 1.71-1.65 (m, 1 H), 1.61-1.49 (m, 2 H), 1.43-1.36 (m, 1 H), 1.29-1.21 (m, 2 H), 1.06 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.8 Hz, 3 H), 0.89 (d, J = 6.6 Hz, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 210.0, 168.4, 144.3, 142.5, 141.7, 134.2, 129.3, 128.3, 125.4, 114.7, 97.7, 97.3, 84.0, 81.2, 74.0, 66.0, 65.8, 59.1, 58.9, 56.4, 56.2, 46.8, 46.0, 41.5, 40.1, 39.2, 34.7, 31.8, 30.9, 29.8, 27.7, 19.9, 19.8, 14.7, 14.4, 12.6. ESI-MS: m/z calcd for C₃₆H₅₈O₁₀: 650; found C₂₆H₅₈O₁₀Na⁺: 673 [M + Na]⁺. ESI-HRMS: m/z calcd for C₃₆H₅₈O₁₀Na⁺ [M + Na]⁺: 673.3922; found: 673.3909.

23

When we were preparing this manuscript and trying to deprotect the MOM group, Füstner group reported the first example of total synthesis of the amphidinolide H1 (1), see ref. 4b.