Stereocontrolled synthesis of (±)-methyl 3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate, a major metabolite of Caribbean sponge, Plakortis halichondrioides, using reactions of alkylidenecarbenes in one pot.
Akiyama, Megumi; Isoda, Yuichi; Nishimoto, Masato; Kobayashi, Aki; Togawa, Daisuke; Hirao, Nobuaki; Kuboki, Atsuhito; Ohira, Susumu.
(±)-Me (2Z,6R*,8R*,9E)-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (I), a major metabolite of the Caribbean sponge, was synthesized in a stereocontrolled manner from γ-caprolactone. The key step was one-pot generation of alkylidenecarbenes at two sites followed by 1,2 hydride shift and intramol. 1,5 C-H insertion.
Research papers (academic journals)
