Enantioselective synthesis of furo[2,3-b]furans, a spongiane diterpenoid substructure

Weisser, Roland and Yue, Weimin and Reiser, Oliver (2005) Enantioselective synthesis of furo[2,3-b]furans, a spongiane diterpenoid substructure. ORGANIC LETTERS, 7 (24). pp. 5353-5356. ISSN 1523-7060, 1523-7052

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Abstract

A short and enantioselective synthesis of cis-fused 5-oxofuro[2,3-b]furans, being found in many spongiane diterpenoid natural products, is reported starting from inexpensive methyl 2-furoate. Moreover, the acid-catalyzed rearrangement of the furo[2,3-b]furan framework A to B is observed for some derivatives, suggesting a simple connection between natural products differing in the absolute configuration of the 3a,6a ring junction.

Item Type: Article
Uncontrolled Keywords: STEREOSELECTIVE-SYNTHESIS; RADICAL CYCLIZATIONS; ASYMMETRIC-SYNTHESIS; PARACONIC ACIDS; NORRISOLIDE; LACTONE; DERIVATIVES; FUROFURAN; FURANS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 23 Apr 2021 06:12
Last Modified: 23 Apr 2021 06:12
URI: https://pred.uni-regensburg.de/id/eprint/35409

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