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Assembly of the Entire Carbon Backbone of a Stereoisomer of the Antitumor Marine Natural Product Hemicalide
Author(s) -
Lecourt Camille,
Dhambri Sabrina,
Yamani Khalil,
Boissonnat Guillaume,
Specklin Simon,
Fleury Etienne,
Hammad Karim,
Auclair Eric,
Sablé Serge,
Grondin Antonio,
Arimondo Paola B.,
Sautel François,
Massiot Georges,
Meyer Christophe,
Cossy Janine,
Sorin Geoffroy,
Lannou MarieIsabelle,
Ardisson Janick
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806327
Subject(s) - natural product , aldol reaction , chess endgame , double bond , chemistry , product (mathematics) , stereochemistry , combinatorial chemistry , organic chemistry , computer science , catalysis , mathematics , artificial intelligence , geometry
A strategy for the assembly of the entire carbon backbone of a stereoisomer of the antitumor marine natural product hemicalide has been investigated. The devised convergent approach relies on Horner–Wadsworth–Emmons and Julia–Kocienski olefination reactions for the construction of the C6=C7 and C34=C35 double bonds, respectively, an aldol reaction to create the C27−C28 bond, and a Suzuki–Miyaura cross‐coupling as the endgame to form the C15−C16 bond.