Studies on C20-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton | Zendy

Amy M. Hamlin | Zendy; David Lapointe | Zendy; Kyle Owens | Zendy; Richmond Sarpong | Zendy

Open Access

Studies on C₂₀-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton

Author(s) -

Amy M. Hamlin,

David Lapointe,

Kyle Owens,

Richmond Sarpong

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo501214b

Subject(s) - chemistry , aldol reaction , skeleton (computer programming) , terpenoid , natural product , total synthesis , bicyclic molecule , stereochemistry , cycloisomerization , formal synthesis , combinatorial chemistry , organic chemistry , catalysis , computer science , programming language

The full details of a synthesis of the hetidine framework of the C20-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6-7-6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines.

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