A Concise Synthesis of the Octalactins
详细信息 查看全文
- 作者：Paul T. O'Sullivan ; Wilm Buhr ; Mary Ann M. Fuhry ; Justin R. Harrison ; John E. Davies ; Neil Feeder ; David R. Marshall ; Jonathan W. Burton ; and Andrew B. Holmes
- 刊名：Journal of the American Chemical Society
- 出版年：2004
- 出版时间：February 25, 2004
- 年：2004
- 卷：126
- 期：7
- 页码：2194 - 2207
- 全文大小：307K
- 年卷期：v.126,no.7(February 25, 2004)
- ISSN：1520-5126
文摘
The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence)and 10% overall yield from commercially available materials. Key steps include the Paterson-Aldol reactionfor the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangementof the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ringlactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.