Submitted by reardonp on Mon, 09/24/2018 - 11:37
TitleEnantioselective Synthesis of (-)-Halenaquinone.
Publication TypeJournal Article
Year of Publication2018
AuthorsGoswami S, Harada K, El-Mansy MF, Lingampally R, Carter RG
JournalAngew Chem Int Ed Engl
Volume57
Issue29
Pagination9117-9121
Date Published2018 Jul 16
ISSN1521-3773
Abstract

The efficient, 12-14 step (LLS) total synthesis of (-)-halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide-catalyzed, Yamada-Otani reaction to establish the C6 all-carbon quaternary stereocenter, (b) multiple, novel palladium-mediated oxidative cyclizations to introduce the furan moiety, and (c) oxidative Bergman cyclization to form the final quinone ring.
DOI10.1002/anie.201805370
Alternate JournalAngew. Chem. Int. Ed. Engl.
PubMed ID29920904