Premium
Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine
Author(s) -
Enomoto Masaru,
Morita Akira,
Kuwahara Shigefumi
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206299
Subject(s) - stille reaction , indole test , total synthesis , diterpene , stereoselectivity , allylic rearrangement , stereochemistry , cyclopropanation , ring (chemistry) , chemistry , natural product , oxidative coupling of methane , organic chemistry , catalysis
Succinct and stereoselective : A high‐yielding two‐step indole ring installation comprising the Stille cross‐coupling and a Pd II ‐mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The tran s‐ anti ‐ trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy‐directed cyclopropanation and allylic selenoxide rearrangement.