Efficient installation and elaboration of C4-C6 fused furan moiety in the total synthesis of teucrium clerodane diterpenoids

Yen-Ku Wu, I. Chia Chen, Jia Liang Zhu, Hsing Jang Liu

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

We previously reported the total synthesis of several Teucrium clerodane diterpenoids including teucvin (1), 12-epi-teucvin (2), montanin A (3) and teuscorolide (4) in a unified Diels-Alder approach. A full account for the tactical installation of the C4-C6 furan ring of 3 from an α,β-unsaturated lactone moiety, and the elaboration of the resulting furan unit into an α,β-unsaturated γ-hydroxyl lactone for preparing 4 is discussed herein. In addition, the transformation of 3 and its 12-epimer into 1 and 2 by the air-mediated furan oxidation reaction is described.

Original languageEnglish
Pages (from-to)2091-2104
Number of pages14
JournalHeterocycles
Volume89
Issue number9
DOIs
StatePublished - 1 Jan 2014

Fingerprint Dive into the research topics of 'Efficient installation and elaboration of C4-C6 fused furan moiety in the total synthesis of teucrium clerodane diterpenoids'. Together they form a unique fingerprint.

Cite this