Collective Total Syntheses of Atisane-Type Diterpenes and Atisine-Type Diterpenoid Alkaloids: (±)-SpiramilactoneB, (±)-Spiraminol, (±)-Dihydroajaconine, and (±)-SpiraminesC andD

The first total syntheses of the architecturally complex atisane-type diterpenes and biogenetically related atisine-type diterpenoid alkaloids (±)-spiramilactoneB, (±)-spiraminol, (±)-dihydroajaconine, and (±)-spiraminesC andD are reported. Highlights of the synthesis include a late-stage biomimetic...

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Bibliographic Details
Published in:Angewandte Chemie 2016-01, Vol.128 (1), p.400-404
Main Authors: Cheng, Hang, Zeng, Fan-Hao, Yang, Xue, Meng, Yin-Juan, Xu, Liang, Wang, Feng-Peng
Format: Article
Language:eng ; ger
Subjects:
Alkaloids
Biomimetics
Chemistry
Construction
Diterpenes
Isomerization
Lactones
Migration
Nucleotide sequence
Synthesis
Transformations
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Summary:The first total syntheses of the architecturally complex atisane-type diterpenes and biogenetically related atisine-type diterpenoid alkaloids (±)-spiramilactoneB, (±)-spiraminol, (±)-dihydroajaconine, and (±)-spiraminesC andD are reported. Highlights of the synthesis include a late-stage biomimetic transformation of spiramilactoneB, a facile formal lactone migration from the pentacyclic skeleton of spiramilactoneE, a highly efficient and diastereoselective 1,7-enyne cycloisomerization to construct the functionalized tetracyclic atisane skeleton, and a tandem retro-Diels-Alder/intramolecular Diels-Alder sequence to achieve the tricyclo[6.2.2.0] ring system.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201508996