Liu C.-W.Yeh T.-C.Chen C.-H.Yu C.-C.Chen C.-S.Hou D.-R.JIH-HWA GUH2021-06-022021-06-022013404020https://www.scopus.com/inward/record.uri?eid=2-s2.0-84874665065&doi=10.1016%2fj.tet.2013.02.015&partnerID=40&md5=31a97cfb7b975c60494272904141fc4bhttps://scholars.lib.ntu.edu.tw/handle/123456789/564798A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated. ? 2013 Elsevier Ltd. All rights reserved.Annonaceous acetogenin; Asymmetric synthesis; C2 Symmetry; Cross metathesis; Ring-closing metathesis[SDGs]SDG31,1' [4,4',7,7' tetrahydro [4,4' bi(1,3 dioxepine )] 7,7' diyl]bis(11 chloroundec 2 en 1 ol); 14,21 diepi squamocin k; 7,7' bis[1 (benzyloxy) 11 chloroundec 2 en 1 yl] 4,4',7,7' tetrahydro 4,4' bi(1,3 dioxepine); 7,7' bis[1 (benzyloxy)allyl] 4,4',7,7' tetrahydro 4,4' bi(1,3 dioxepine); 7,7' bis[1 (methoxymethoxy)allyl] 4,4',7,7' tetrahydro 4,4' bi(1,3 dioxepine); 7,7' bis[11 chloro 1 (methoxymethoxy)undec 2 en 1 yl] 4,4',7,7' tetrahydro 4,4' bi(1,3 dioxepine); acetogenin; lactone; squamocin; unclassified drug; article; drug synthesis; nucleophilicity; priority journal; prostate cancer; ring closing metathesis; skeleton; substitution reactionjournal article10.1016/j.tet.2013.02.0152-s2.0-84874665065