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Synlett 2012; 23(8): 1213-1216
DOI: 10.1055/s-0031-1290803
DOI: 10.1055/s-0031-1290803
letter
Stereoselective Total Syntheses of Insect Juvenile Hormones JH 0 and JH I
Further Information
Publication History
Received: 08 December 2011
Accepted after revision: 27 February 2012
Publication Date:
20 April 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201208/lookinside/thumbnails/10.1055-s-0031-1290803-1.jpg)
Abstract
Total syntheses of juvenile hormones JH 0 and JH I have been achieved by a new iterative enol tosylate homologation strategy.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
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- 12 The olefin geometry was confirmed by NOE experiments of the synthetic JH 0 and JH I (see Supporting Information)
-
The use of the unactivated enol tosylate in the cross-coupling reaction has been discussed, see:
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- 14 The optical purity was confirmed by the total synthesis of JH 0 and JH I, and comparison of the optical rotations of the synthetic natural products with those of authentic data shown in below
- 15 Analytical Data of JH 0 (1): [α]D 18 +13.4 (c 0.8, MeOH) [lit. 5d [α]D + 13.8 (c 0.92, MeOH)]. 1H NMR (400 MHz, CDCl3): δ = 5.61 (s, 1 H), 5.10 (br, 1 H), 3.68 (s, 3 H), 2.71 (dd, J = 6.6, 5.6 Hz, 1 H), 2.18–2.03 (m, 10 H), 1.63–1.48 (m, 4 H), 1.27 (s, 3 H), 1.07 (t, J = 7.6 Hz, 3 H), 1.00 (t, J = 7.6 Hz, 3 H), 0.96 (t, J = 7.6 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 166.8, 165.7, 141.2, 123.1, 114.5, 64.6, 61.8, 50.7, 38.1, 33.3, 27.2, 25.8, 25.7, 25.3, 23.2, 21.6, 13.1, 12.9, 9.6. IR (neat): 2970, 2353, 1720, 1644, 1461, 1209, 1149, 761 cm–1. HRMS–FAB: m/z calcd for C19H33O3 [M + H]+: 309.2430; found: 309.2421
- 16 Analytical Data of JH I (2): [α]D 18 +14.4 (c 0.98, MeOH) [lit.5a,e [α]D 22.5 +14.5 (c 0.78, MeOH)]. 1H NMR (400 MHz, CDCl3): δ = 5.66 (d, J = 0.6 Hz 1 H), 5.08 (t, J = 6.3 Hz, 1 H), 3.68 (s, 3 H), 2.71 (dd, J = 7.2, 6.0 Hz, 1 H), 2.18–2.03 (m, 8 H), 2.16 (d, J = 0.6 Hz, 3 H), 1.63–1.48 (m, 4 H), 1.27 (s, 3 H), 0.99 (t, J = 7.2 Hz 3 H), 0.97 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 167.2, 159.9, 141.3, 122.9, 115.3, 64.6, 61.8, 50.8, 41.1, 33.3, 27.2, 25.8, 25.6, 23.1, 21.6, 18.8, 13.1, 9.7. IR (neat): 2968, 2360, 1720, 1650, 1457, 1125, 1149, 770 cm–1. HRMS–FAB: m/z calcd for C18H31O3 [M + H]+: 295.2273; found: 295.2270