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Biomimetic Total Synthesis of (±)‐Verrubenzospirolactone
Author(s) -
Lam Hiu C.,
Pepper Henry P.,
Sumby Christopher J.,
George Jonathan H.
Publication year - 2017
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.201700114
Subject(s) - stereocenter , intramolecular force , total synthesis , cascade , stereochemistry , chemistry , cascade reaction , diels–alder reaction , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , chromatography
A five‐step total synthesis of (±)‐verrubenzospirolactone has been achieved using a biomimetic, intramolecular Diels–Alder reaction of a 2 H ‐chromene to form two rings and four stereocenters in the final step. This Diels–Alder reaction occurs spontaneously at 30 °C “on‐water”, and thus suggests that it is likely to be non‐enzymatic in nature. The structure of (±)‐verrubenzospirolactone was also used to inspire a quadruple cascade reaction to generate seven stereocenters, four rings, three C−C bonds, and two C−O bonds in one step.