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In this article, we report the synthesis of (±)-5- epi -vetiverianine A. The key reactions, including a rhodium-catalyzed coupling reaction and an oxidative phenolic cyclization, allow for efficient and stereoselective access to (±)-5- epi -vetiverianine A in 11 steps, and in 20% overall yield. The stereochemistry is confirmed by NOE studies. [ABSTRACT FROM AUTHOR]

Herein, we describe the first total synthesis of cochlearol B, a meroterpenoid natural product featuring a 4/5/6/6/6‐fused pentacyclic structure. Key steps, oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition, which constructed the pentacyclic structure in highly stereoselective manner, allowed efficient access to cochlearol B with the longest linear sequence of 16 steps, and in 9 % overall yield. Single‐crystal X‐ray crystallographic analysis clearly confirmed the stereochemistry of cochlearol B. [ABSTRACT FROM AUTHOR]

The synthesis of a CD ring analogue of aconitine is described. The SmI 2 -mediated reductive cyclization of an α,β-epoxyketone with a pendant formyl group allowed for stereocontrolled construction of the bicyclo[3.2.1]octane framework. Further oxidative manipulation installed oxygen functionalities with the desired stereochemistry, thus completing the synthesis of the CD ring fragment of aconitine. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • A total synthesis of granulodione is described. • The carbon framework was constructed by the SmI 2 -mediated reductive cyclization. • Further oxidation completed a total synthesis of granulodione. Abstract In this paper, we report the total synthesis of a sesquiterpene, granulodione, having a 15-norilludane skeleton. The coupling of two fragments 3 and 4 via aldol condensation, followed by Saegusa oxidation, SmI 2 -mediated cyclization, and oxidation enabled expeditious and efficient synthesis of granulodione. [ABSTRACT FROM AUTHOR]