Studies toward the total synthesis of armatol F: Stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton

Kenshu Fujiwara, Yuta Hirose, Daisuke Sato, Hidetoshi Kawai, Takanori Suzuki

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has a solitary oxepane (A-ring) and a fused tricyclic ether moiety (BCD-ring). The A-ring features a rare cis-relationship between the hydroxy group at the quaternary carbon C6 and the carbon chain at C7. As part of our program toward the total synthesis of armatol F, a new stereoselective method for the construction of the C6 and C7 stereocenters has been developed based on chirality-transferring Ireland-Claisen rearrangement. The A-ring skeleton has also been synthesized from the rearrangement product by a process including ring-closing olefin metathesis.

Original languageEnglish
Pages (from-to)4263-4266
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number32
DOIs
Publication statusPublished - 11 Aug 2010

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