Expedient Construction of the Hexacycle of Franchetine

Franchetine, a unique 7,17‐seco type of norditerpenoid alkaloid, possesses a highly congested polycyclic architecture coupled with nine stereogenic centers. Here we present an efficient synthetic approach for the intact hexacyclic framework of franchetine from the known tricyle 16 in 20 steps. The s...

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Published inChemistry, an Asian journal Vol. 13; no. 8; pp. 955 - 958
Main Authors Lv, Zhengchao, Gao, Lingzhi, Cheng, Chuanxu, Niu, Wei, Wang, Jian‐Li, Xu, Liang
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 16.04.2018
Subjects
Chemistry
franchetine
natural products
norditerpenoid alkaloids
radical cyclization
Wagner–Meerwein rearrangement
natural products
franchetine
radical cyclization
norditerpenoid alkaloids
Wagner-Meerwein rearrangement
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Summary:Franchetine, a unique 7,17‐seco type of norditerpenoid alkaloid, possesses a highly congested polycyclic architecture coupled with nine stereogenic centers. Here we present an efficient synthetic approach for the intact hexacyclic framework of franchetine from the known tricyle 16 in 20 steps. The synthesis features a diastereoselective 6‐exo‐tet radical cyclization for construction of ring A and a unique oxidative Wagner–Meerwein‐type rearrangement to realize the functionalized [3.2.1] bridging ring CD. Making your own CD: An efficient synthetic approach for the intact hexacyclic framework of franchetine from the known tricyle 16 in 20 steps is reported. The synthesis features a diastereoselective 6‐exo‐tet radical cyclization for construction of ring A and a unique oxidative Wagner–Meerwein‐type rearrangement to realize the functionalized [3.2.1] bridging ring CD.
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ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201800116