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Paper | Regular issue | Vol 89, No. 9, 2014, pp.2091-2104
Published online, 31st July, 2014
DOI: 10.3987/COM-14-13045
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,* and Hsing-Jang Liu*

*Department of Chemistry, National Dong Hwa University, 1, Sec. 2, Hsueh Rd., Shou-Feng, Hualien 974, Taiwan, R.O.C.

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.