Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D | Zendy

Cheng Hang | Zendy; Zeng FanHao | Zendy; Yang Xue | Zendy; Meng YinJuan | Zendy; Xu Liang | Zendy; Wang FengPeng | Zendy

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Collective Total Syntheses of Atisane‐Type Diterpenes and Atisine‐Type Diterpenoid Alkaloids: (±)‐Spiramilactone B, (±)‐Spiraminol, (±)‐Dihydroajaconine, and (±)‐Spiramines C and D

Author(s) -

Cheng Hang,

Zeng FanHao,

Yang Xue,

Meng YinJuan,

Xu Liang,

Wang FengPeng

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201508996

Subject(s) - stereochemistry , chemistry , intramolecular force , ring (chemistry) , terpenoid , enyne , cycloisomerization , diterpene , total synthesis , tandem , organic chemistry , catalysis , materials science , composite material

The first total syntheses of the architecturally complex atisane‐type diterpenes and biogenetically related atisine‐type diterpenoid alkaloids (±)‐spiramilactone B, (±)‐spiraminol, (±)‐dihydroajaconine, and (±)‐spiramines C and D are reported. Highlights of the synthesis include a late‐stage biomimetic transformation of spiramilactone B, a facile formal lactone migration from the pentacyclic skeleton of spiramilactone E, 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.

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