Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1−C19 Sector
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- 作者：Sipak Joyasawal ; Stephen D. Lotesta ; N. G. Akhmedov ; Lawrence J. Williams
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：March 5, 2010
- 年：2010
- 卷：12
- 期：5
- 页码：988-991
- 全文大小：290K
- 年卷期：v.12,no.5(March 5, 2010)
- ISSN：1523-7052
文摘
The synthesis of a C1−C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.