Premium
Total Synthesis of Diaporthichalasin by Using the Intramolecular Diels–Alder Reaction of an α,β‐Unsaturated γ‐Hydroxylactam in Aqueous Media
Author(s) -
Shionozaki Nobuhiro,
Iwamura Naoki,
Tanaka Ryo,
Makino Kimiko,
Uchiro Hiromi
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201201230
Subject(s) - intramolecular force , decalin , diels–alder reaction , chemistry , lactam , diene , stereochemistry , aqueous medium , total synthesis , aqueous solution , organic chemistry , catalysis , natural rubber
The first total synthesis of diaporthichalasin has been successfully achieved and complete structure elucidation , including the absolute configuration, was also accomplished. The intramolecular Diels–Alder (IMDA) reaction between the diene side chain on the decalin skeleton and α,β‐unsaturated γ‐hydroxy‐γ‐lactam in aqueous media was effectively employed as the key step. From this synthetic study, we found that α,β‐unsaturated γ‐hydroxy‐γ‐lactam is an essential precursor for the construction of the diaporthichalasin‐type pentacyclic skeleton. This important finding strongly suggests that this route is involved in the biosynthetic pathway for diaporthichalasin.