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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Published inAngewandte Chemie International Edition Vol. 57; no. 4; pp. 942 - 946
Main Authors Zhang, Yuebao, Guo, Qianyou, Sun, Xianwei, Lu, Ji, Cao, Yanjun, Pu, Qiang, Chu, Zhiwen, Gao, Lu, Song, Zhenlei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.01.2018
Subjects
Chemistry
Chemistry, Multidisciplinary
cyclization
natural products
Physical Sciences
pyrans
rearrangements
Science & Technology
total synthesis
pyrans
PROTEIN-KINASE-C
ANALOGS
ALLYLATION
ANTINEOPLASTIC AGENTS
ALDEHYDES
cyclization
ALCOHOLS
natural products
ANTITUMOR MACROLIDES
rearrangements
GEMINAL BIS(SILANE)
total synthesis
BETA-HYDROXY KETONES
SELECTIVITY
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201711452