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Atroposelective Synthesis of Isoriccardin C through a C−H Activated Heck Type Macrocyclization
Author(s) -
Marx Lisa,
Lamberty Daniel,
Choppin Sabine,
Colobert Françoise,
Speicher Andreas
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100017
Subject(s) - chemistry , enantiopure drug , heck reaction , combinatorial chemistry , oxidative coupling of methane , stereochemistry , molecule , enantioselective synthesis , organic chemistry , catalysis , palladium
Macrocyclization is typically the key step in syntheses of cyclophane‐type natural products. Considering compounds with axially chiral biaryl moieties, the control of atroposelectivity is essential for biological activity and is synthetically challenging. Herein we report on atroposelective macrocyclization involving an oxidative Heck type process and enabling the first atropo‐enantiopure synthesis of isoriccardin C. A chiral sulfinyl auxiliary in the ortho‐position of a biaryl axis (still flexible) was used to induce a C−H activated atropodiastereoselective oxidative Heck coupling (>98 % de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target molecule with >98 % ee as well.