Subscribe to RSS
DOI: 10.1055/s-2006-933141
Enantioselective Synthesis of cis-3-Oxy-2,2,6,6-tetrasubstituted Tetrahydropyrans
Publication History
Publication Date:
14 March 2006 (online)
Abstract
A synthesis of cis-3-oxy-2,2,6,6-tetrasubstituted tetrahydropyrans has been achieved in an easy and straightforward way.
Key words
Sharpless epoxidation - nitriles - tetrahydropyrans - cyclisation - iodine
-
1a
Elliott MC. J. Chem. Soc., Perkin Trans. 1 2002, 2301 -
1b
Elliott MC.Williams E. J. Chem. Soc., Perkin Trans. 1 2001, 2303 -
1c
Elliott MC. J. Chem. Soc., Perkin Trans. 1 2000, 1291 - 2
Grabley S.Hamman P.Hutter K.Kirsch R.Kluge H.Thericke R. J. Antibiot. 1992, 45: 1176 - 3
Paterson I.Chen D.Coster M.Acena J.Bach J.Gibson K.Keown L.Oballa R.Trieselmann T.Wallace D.Hodgson A.Norcross R. Angew. Chem. Int. Ed. 2001, 40: 4055 - 4
Lin YY.Risk M.Van Engen D.Clardy J.Golik J.James JC.Nakanishi K. J. Am. Chem. Soc. 1981, 103: 6773 - 5
Murata M.Naoki H.Matsunaga S.Satake M.Yasumoto T. J. Am. Chem. Soc. 1994, 116: 7098 - 6
Hall JG.Reiss JA. Aust. J. Chem. 1986, 39: 1401 -
7a
Uemura D.Takahashi K.Yamamoto T.Katayama C.Tanaka J.Okumura Y.Hirata Y. J. Am. Chem. Soc. 1985, 107: 4796 -
7b
Hirata Y.Uemura D. Pure Appl. Chem. 1986, 58: 701 -
7c
Bai R.Paull KD.Herald CL.Pettit GR.Malspeis L.Hamel E. J. Biol. Chem. 1991, 266: 15882 -
7d Halichondrin B and homohalichondrin B were also isolated from Acinella sponge, see:
Pettit GR.Herald CL.Boyd MR.Leet JE.Dufresne C.Doubek DL.Schmidt JM.Cerny RL.Hooper JNA.Rutzler KC. J. Med. Chem. 1991, 34: 3339 -
7e Iso-homohalichondrin has been isolated from Lissodendoryx sponge, see:
Hart JB.Blunt JW.Munro HG. J. Org. Chem. 1996, 61: 2888 ; and references cited therein - 8
Tan DS.Schreiber SL. Tetrahedron Lett. 2000, 41: 9509 - 9
Betancor C.Dorta RL.Freire R.Prangé T.Suárez E. J. Org. Chem. 2000, 65: 8822 - 10
Carrillo R.Martin VS.Martin T. Tetrahedron Lett. 2004, 45: 5215 - 11
Gung BW.Francis MB. J. Org. Chem. 1993, 58: 6177 -
12a
Martin VS.Nuñez MT.Ramirez MA.Soler MA. Tetrahedron Lett. 1990, 31: 763 -
12b
Martin VS.Palazon JM. Tetrahedron Lett. 1992, 33: 2399 -
12c
Betancort JM.Martin VS.Padron JM.Palazón JM.Ramirez MA.Soler MA. J. Org. Chem. 1997, 62: 4570 -
12d
Ramirez MA.Padron JM.Palazón JM.Martin VS. J. Org. Chem. 1997, 62: 4584 - 13
Gevorgyan V.Kadota I.Yamamoto Y. Tetrahedron Lett. 1993, 34: 1313 - 14
Hoffmann RW.Münster I. Tetrahedron Lett. 1995, 36: 1431 - 15
Avery TD.Caiazza D.Culbert JA.Taylor DK.Tiekink ERT. J. Org. Chem. 2005, 70: 8344 - 16
Diez D.Marcos IS.Basabe P.Romero RE.Moro RF.Lumeras W.Rodriguez L.Urones JG. Synthesis 2001, 1013 - 17
Katsuki T.Martín VS. Org. React. 1996, 48: 1 - 18
Wright JN.Calder MR.Akhtar M. J. Chem. Soc., Chem. Commun. 1985, 1733 - 19
Yoon NM.Gyoung YS. J. Org. Chem. 1985, 50: 2443 - 20
Labelle M.Morton HE.Guindon Y.Springer JP. J. Am. Chem. Soc. 1988, 110: 4533 -
22a
Mancuso AJ.Huang S.Swern D. J. Org. Chem. 1978, 43: 2480 -
22b
Mancuso AJ.Huang S.Swern D. Synthesis 1981, 165 - 23
Díez D.Kotecha NR.Ley SV.Mantegani S.Menéndez JC.Organ HM.White AD.Banks BJ. Tetrahedron 1992, 48: 7899 - 24
White JD.Mitchell AA.Choudhry SC.Dhingra OP.Gray BD.Kang M.Kuo S.Whittle AJ. J. Am. Chem. Soc. 1989, 111: 790 -
25a
Gung BW.Wolf MA.Zhu Z. J. Org. Chem. 1993, 58: 3350 -
25b
Gung BW.Wolf MA. J. Org. Chem. 1993, 58: 7038 -
25c See also:
Labelle M.Guindon Y. J. Am. Chem. Soc. 1989, 111: 2204
References and Notes
Spectroscopic Data for Compound 12.
[α]D
20 +22.5 (c 1.0, CHCl3). IR (film): 3460 (br), 2970-2870, 1454, 1377, 1221, 1069, 974, 731, 696 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.46-7.30 (5 H, m, Ph), 4.85 (1 H, dd, J = 3.4, 10.1 Hz, H-1′), 4.58 (1 H, d, J = 10.8 Hz, OCH2Ph, HA), 4.48 (1 H, d, J = 10.8 Hz, OCH2Ph, HB), 4.09 (1 H, m, HA-2′), 3.94 (1 H, m, HB-2′), 3.43 (1 H, m, H-3), 2.05-1.85 (4 H, m, H-4, H-5), 1.51 (3 H, s, H-9), 1.26, 1.22 (3 H each, s, H-7 and H-8) ppm. 13C NMR (100 MHz, CDCl3): δ = 18.33 (C-4), 20.13 (C-9), 27.44 (C-7), 29.34 (C-5), 32.81 (C-8), 39.12 (C-1′), 66.70 (C-2′), 71.15 (PhCH2), 74.04 (C-6), 75.98 (C-3), 127.47 (Ph
para
), 127.69 (Ph
ortho
), 128.25 (Ph
meta
), 138.45 (Ph
ipso
) ppm. HMRS (EI): m/z calcd for C17H26O3I: 405.0927 [M + H]+; found: 405.0944.