Stereoselective Synthesis of
Methyl Spongoate, a New Steroid with Potent Antitumor
Activities

Jing-Xu Gong; Ze-Hong Miao; Li-Gong Yao; Jian Ding; Tibor Kurtán; Yue-Wei Guo

doi:10.1055/s-0029-1218567

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Synlett 2010(3): 480-482
DOI: 10.1055/s-0029-1218567

LETTER

Stereoselective Synthesis of Methyl Spongoate, a New Steroid with Potent Antitumor Activities

Jing-Xu Gong^a, Ze-Hong Miao^a, Li-Gong Yao^a, Jian Ding^a, Tibor Kurtán^b, Yue-Wei Guo*^a
^a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P. R. of China
Fax: +86(21)50805813; e-Mail: ywguo@mail.shcnc.ac.cn;
^b Department of Organic Chemistry, University of Debrecen, PO Box 20, 4010 Debrecen, Hungary

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Publication History

Received 11 September 2009
Publication Date:
11 December 2009 (online)

Abstract
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Abstract

The stereoselective synthesis of methyl spongoate, a naturally occurring new steroid derivative with an unusual C-20 methoxycarbonyl group and potent antitumor activities, was achieved starting from the commercially available pregnenolone acetate in 11% overall yield.

Key words

steroids - methyl spongoate - stereoselective synthesis - diastereoselective alkylation - cytotoxicity

Supporting Information

References

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10

Characteristic Spectroscopic Data of Compound 8
[α]_D ^²0 +55.0 (c 0.45, CHCl₃). ^¹H NMR (400 MHz, CDCl₃): δ = 3.63 (s, 3 H), 0.98 (s, 3 H), 0.83 (d, J = 6.6 Hz, 3 H), 0.82 (d, J = 6.6 Hz, 3 H), 0.69 (s, 3 H). ^¹³C NMR and DEPT (100 MHz, CDCl₃): δ = 11.0 (CH₃), 12.1 (CH₃), 21.2 (CH₂), 22.3 (CH), 22.7 (CH), 23.7 (CH₂), 25.1 (CH₂), 27.1 (CH₂), 27.8 (CH), 28.8 (CH₂), 31.6, (CH₂), 32.2 (CH₂), 35.3 (CH), 35.6 (C), 37.4 (CH₂), 38.2 (CH₂), 38.8 (CH₂), 42.1 (C), 44.7 (CH₂), 46.6 (CH), 47.3 (CH), 51.0 (CH₃), 52.7 (CH), 53.7 (CH), 55.4 (CH), 176.7 (C), 212.2 (C). HRMS: m/z calcd for C₂₈H₄₆O₃ [M⁺]: 430.3447; found: 430.3435.

Supplementary Material

Supporting Information