Synthesis of the myrmicarin family of natural products

杨梅苷家族天然产物的合成

• 批准号: 6789741
• 负责人: Scott Alan Snyder
• 金额: $ 4.11万
• 依托单位: HARVARD UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2004
• 资助国家: 美国
• 起止时间: 2004-09-01 至 2006-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6789741
• 关键词: alkaloids; arthropod poison; biological products; biosynthesis; chemical synthesis; postdoctoral investigator; stereochemistry

DESCRIPTION (provided by applicant): Despite the unique and impressive complexity of the higher-order members of the myrmicarin family of natural products and their established potential to serve as valuable leads for the study of chemical biology, these secondary metabolites have remained unanswered synthetic challenges for nearly a decade. The absence of a cohesive biosynthetic pathway accounting for their formation could potentially explain this state of affairs. In this proposal, a unifying biogenetic hypothesis is advanced which outlines a clear method to accomplish the synthesis of all these compounds from two key starting materials, one of which is a simpler member of the myrmicarin family. Carefully considered synthetic pathways to the proposed materials for this sequence, facilitated by a series of designed cascade reactions and new synthetic methodologies, will enable its evaluation. The overall significance of this work resides in its promise to establish presently missing biosynthetic links for the myrmicarin family, to provide both natural and designed molecules that can serve as tools for the study of chemical biology, and to contribute generally to the advancement of synthetic organic chemistry.

描述(由申请人提供)： 尽管天然产物桃金娘内酯家族的高级成员具有独特而令人印象深刻的复杂性，并且它们有可能成为化学生物学研究的有价值的线索，但近十年来，这些次生代谢物仍然是一个悬而未决的合成挑战。它们的形成缺乏内聚的生物合成途径，这可能会解释这种情况。在这一建议中，提出了一个统一的生物发生假说，该假说概述了一种明确的方法，可以从两个关键的起始原料合成所有这些化合物，其中一个是桃金娘红素家族中较简单的成员。在一系列设计的级联反应和新的合成方法的推动下，经过仔细考虑的合成路径将使其能够进行评估。这项工作的总体意义在于它有望为肉豆蔻素家族建立目前缺失的生物合成环节，提供可用作化学生物学研究工具的天然和设计分子，并总体上为合成有机化学的进步做出贡献。