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- Title
Bioinspired Total Synthesis of Homodimericin A.
- Authors
Huang, Jun; Gu, Yueqing; Guo, Kai; Zhu, Lei; Lan, Yu; Gong, Jianxian; Yang, Zhen
- Abstract
Homodimericin A is a remarkable fungal metabolite. This highly oxygenated racemic unsaturated polyketide poses a significant synthetic challenge owing to its sterically demanding central cagelike core containing eight contiguous stereogenic centers (including three quaternary stereocenters) and several carbonyl functionalities. On the basis of its proposed biogenetic synthesis, we designed a total synthesis of homodimericin A that proceeds in seven steps and features a double Michael reaction, an intramolecular Diels-Alder reaction, and an ene reaction.
- Subjects
POLYKETIDES; FUNGAL metabolites; FUNGI physiology; MICROBIAL metabolites; CARBONYL compounds
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 27, p7998
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201702768