Mukaiyama Aldol Strategy Towards the Leptosin Alkaloids

向山羟醛策略针对瘦素生物碱

• 批准号: 6791785
• 负责人: AARON D WROBLESKI
• 金额: $ 4.11万
• 依托单位: UNIVERSITY OF CALIFORNIA-IRVINE
• 依托单位国家: 美国
• 财政年份: 2004
• 资助国家: 美国
• 起止时间: 2004-04-05 至 2007-04-04
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6791785
• 关键词: alcohols; aldehydes; alkaloids; biological products; chemical reaction; chemical structure function; chemical synthesis; method development; piperazines; postdoctoral investigator; pyrrolidines; stereochemistry

DESCRIPTION (provided by applicant): The leptosins are a class of natural products presenting remarkable molecular complexity and potent cytotoxic and antitumor activity. Thus far, no reports documenting the total synthesis of any of these alkaloids has been published. One of the more complex challenges such a synthesis must address is the stereocontrolled formation of the central bispyrrolidinoindoline ring system containing consecutive all-carbon quaternary centers and two secondary alcohols. It is proposed that using a one-pot double Mukaiyama aldol reaction will allow for the installation of both quaternary centers and adjacent secondary alcohols. Before this reaction can be used to install the above stereogenic centers, it is necessary to understand the stereocontrolling elements of the reaction. With that, before undertaking any total syntheses preliminary studies will focus on examining how varying the structures of the reactive components of the Mukaiyama aldol dictate reaction stereocontrol. Once the stereocontrolling elements of this reaction are understood, a proposal towards completing the total syntheses of leptosins C and K will be presented.

描述（由申请人提供）：