Asymmetric Total Synthesis of (-)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family

Takahiro Suzuki; Soichiro Watanabe; Muhammet Uyanik; Kazuaki Ishihara; Susumu Kobayashi; Keiji Tanino

doi:10.1021/acs.orglett.8b01502

Asymmetric Total Synthesis of (-)-Maldoxin, a Common Biosynthetic Ancestor of the Chloropupukeananin Family

Org Lett. 2018 Jul 6;20(13):3919-3922. doi: 10.1021/acs.orglett.8b01502. Epub 2018 Jun 8.

Authors

Takahiro Suzuki¹, Soichiro Watanabe², Muhammet Uyanik³, Kazuaki Ishihara³, Susumu Kobayashi⁴, Keiji Tanino¹

Affiliations

¹ Department of Chemistry, Faculty of Science , Hokkaido University , Sapporo , 060-0816 Hokkaido , Japan.
² Graduate School of Chemical Sciences and Engineering , Hokkaido University , Sapporo , 060-0816 Hokkaido , Japan.
³ Graduate School of Engineering , Nagoya University , Furo-cho, Chikusa , Nagoya 464-8603 , Japan.
⁴ Faculty of Pharmaceutical Sciences , Tokyo University of Science , 2641 Yamazaki , Noda , Chiba 278-8510 , Japan.

PMID: 29883129
DOI: 10.1021/acs.orglett.8b01502

Abstract

The total synthesis of pestheic acid based on an intramolecular S_NAr reaction without a nitro group and the asymmetric synthesis of (-)-maldoxin by a catalytic enantioselective oxidative dearomatization of pestheic acid are described. The reactivity of (-)-maldoxin as a diene in the Diels-Alder reaction is also investigated.

Publication types

Research Support, Non-U.S. Gov't