1. Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system
- Author
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Kunkai Wang, Zhixiang Xie, Xiangchuang Tan, and Zhezhe Xu
- Subjects
010405 organic chemistry ,Chemistry ,Stereochemistry ,Dodecane ,Organic Chemistry ,Regioselectivity ,Total synthesis ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Stereocenter ,chemistry.chemical_compound ,Aldol reaction ,Intramolecular force ,Drug Discovery ,Moiety - Abstract
The bowl-shaped tricyclo[6.3.1.04,12]dodecane moiety is the core feature of cephalotane-type diterpenoids. As part of our efforts directed towards a total synthesis of mannolide B, the bowl-shaped tricyclo[6.3.1.04,12]dodecane skeleton, a common intermediate of cephalotane-type diterpenoids bearing up to five contiguous stereocenters including two quaternary carbon centers had been constructed. The synthetic strategy was enabled by an efficient application of oxidative dearomatization/intramolecular Diels-Alder reaction to access highly functionalized building block with the tricyclo[5.2.2.02,6]undecane unit from commercially available materials. The key feature was firstly used the cyclic olefins with secondary alcohol as dienophile for the intramolecular inverse electron demand Diels-Alder reaction. Further synthetic studies led to construct ring D by a regioselective Aldol reaction.
- Published
- 2020
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