酶促和对映选择性方法合成 1,2-环并[2.2.2]辛烷和相关三环骨架。

Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks.

机构信息

Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

出版信息

Org Biomol Chem. 2010 Feb 21;8(4):751-4. doi: 10.1039/b921600f. Epub 2009 Dec 7.

DOI:10.1039/b921600f

PMID:20135028

Abstract

New and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol (X = I) and its 6-methylated derivative into either antipodal form of compounds embodying the tricyclic frameworks of terpenoids . Key steps include intramolecular Diels-Alder (IMDA) and (in some cases) singlet or triplet-based photochemical processes.

摘要

现描述了用于将酶促衍生的对映纯顺-1,2-二氢邻苯二酚（X = I）及其 6-甲基衍生物转化为体现萜类三环骨架的对映异构体形式的化合物的新的简单方案。关键步骤包括分子内 Diels-Alder（IMDA）和（在某些情况下）单重态或三重态基光化学反应。