Open AccessTotal Synthesis of Limaol
Author(s) -
Stephan N. Hess,
Xiaobin Mo,
Cornelia Wirtz,
Alois Fürstner
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.0c12948
Subject(s) - chemistry , stille reaction , polyketide , methylene , stereochemistry , substrate (aquarium) , catalysis , combinatorial chemistry , organic chemistry , biosynthesis , enzyme , oceanography , geology
A nonthermodynamic array of four skipped methylene substituents on the hydrophobic tail renders limaol, a C40-polyketide of marine origin, unique in structural terms. This conspicuous segment was assembled by a two-directional approach and finally coupled to the polyether domain by an allyl/alkenyl Stille reaction under neutral conditions. The core region itself was prepared via a 3,3'-dibromo-BINOL-catalyzed asymmetric propargylation, a gold-catalyzed spirocyclization, and introduction of the southern sector via substrate-controlled allylation as the key steps.