Asymmetric Total Synthesis of Clavulactone

克拉内酯的不对称全合成

• 批准号: 6646167
• 负责人: Jason Kingsbury
• 金额: $ 3.97万
• 依托单位: HARVARD UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2003
• 资助国家: 美国
• 起止时间: 2003-05-01 至 2005-06-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6646167
• 关键词: antineoplastics; carbopolycyclic compound; chemical addition; chemical reaction; chemical synthesis; coral; cyclic compound; diterpenes

DESCRIPTION (provided by applicant): Clavulactone (1) is an unusual dolabellane diterpene isolated from the Pacific soft coral Clavularia viridis. Its unprecedented tricyclic structure and antitumor activity motivate the studies described in this proposal. Daunting challenges posed by 1 include the remote stereocenter at C8, the quaternary carbon center at C1, and the potentially strained eleven-membered medium ring. Our synthesis plan incorporates macrocyclic stereocontrol, catalytic asymmetric conjugate addition of an alkyl metal reagent, and a fascinating intramolecular hetero Diels-Alder reaction.

描述（由申请人提供）：克拉维酮（1）是一种从太平洋软珊瑚clavularia viridis分离出来的异常的dolabellane ditrene。其前所未有的三环结构和抗肿瘤活性激发了本提案中描述的研究。 1提出的艰巨挑战包括C8处的远程立体中心，C1的第四纪碳中心以及潜在的11个元元中环。我们的合成计划结合了大环立体控制，催化不对称结合物的添加烷基金属试剂，以及令人着迷的分子内异二二二烷二烷 - alder反应。