Total Synthesis of Bryostatin 8 Using an Organosilane‐Based Strategy

Convergent total synthesis of bryostatin 8 has been accomplished by an organosilane‐based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)‐based [1,5]‐Brook rearrangement, and the B ring through geminal bis(silane)‐based Prins cyclization, thus efficiently joining...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-01, Vol.57 (4), p.942-946
Main Authors: Zhang, Yuebao, Guo, Qianyou, Sun, Xianwei, Lu, Ji, Cao, Yanjun, Pu, Qiang, Chu, Zhiwen, Gao, Lu, Song, Zhenlei
Format: Article
Language:English
Subjects:
cyclization
natural products
pyrans
rearrangements
total synthesis
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Summary:Convergent total synthesis of bryostatin 8 has been accomplished by an organosilane‐based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)‐based [1,5]‐Brook rearrangement, and the B ring through geminal bis(silane)‐based Prins cyclization, thus efficiently joining the northern and southern parts of the molecule. The eight ball: Convergent total synthesis of bryostatin 8 has been accomplished using an organosilane‐based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)‐based [1,5]‐Brook rearrangement, and the B ring through a geminal bis(silane)‐based Prins cyclization, thus efficiently joining the northern and southern parts of the molecule.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201711452