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Total Synthesis of the Hamigerans
Author(s) -
Li Xiaojun,
Xue Dongsheng,
Wang Cheng,
Gao Shuanhu
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604070
Subject(s) - total synthesis , stereochemistry , ring (chemistry) , chemistry , cleavage (geology) , sequence (biology) , oxidative cleavage , biology , organic chemistry , biochemistry , catalysis , fracture (geology) , paleontology
The first total synthesis of hamigerans D, G, L, and N–Q has been accomplished. A convergent approach was used to build the basic tricarbocyclic ring system bearing a 5‐6‐6 structure. A sequence of oxidative cleavage, homologation, and ring regeneration provided access to the 5‐7‐6 skeleton of hamigeran G. Based on the biogenetic hypothesis, elegant and highly efficient biomimetic transformations of hamigeran G into hamigerans D, N–Q, and L were achieved.
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