286930-15-2Relevant academic research and scientific papers
Asymmetric total synthesis of halicholactone
Takemoto, Yoshiji,Baba, Yasutaka,Saha, Goutum,Nakao, Syusuke,Iwata, Chuzo,Tanaka, Tetsuaki,Ibuka, Toshiro
, p. 3653 - 3656 (2000)
The total synthesis of halicholactone by using the chirality of (diene)Fe(CO)3 complexes was reported. The key steps of the synthesis include catalytic asymmetric alkylation, regio- and stereoselective phenylsulfenylation, regio- and stereoselective cyclopropanation and formation of a nine-membered lactone by ring-closing metathesis. (C) 2000 Elsevier Science Ltd.
Asymmetric total synthesis of halicholactone
Baba,Saha,Nakao,Iwata,Tanaka,Ibuka,Ohishi,Takemoto
, p. 81 - 88 (2007/10/03)
The asymmetric total synthesis of the marine metabolite, halicholactone 1, is described. The bisatlylic triol 6 with three chiral centers at C8, C12, and C15 was constructed by [2,3]-sigmatropic rearrangement of the sulfoxide 18, which was prepared stereoselectively using the chirality of (diene)Fe(CO)3 complexes. Introduction of the trans-substituted cyclopropane subunit into 21 was successfully achieved using the modified regio- and stereoselective Simmons - Smith reaction. The use of RCM (ring-closing metathesis) methodology (4 → 35) was pivotal for the formation of a nine-membered unsaturated lactone fragment of halicholactone 1. As this approach is flexible and stereoselective, other oxylipins could be synthesized by the protocol described herein.
