Total synthesis of 14,21-diepi-squamocin-K
Journal
Tetrahedron
Journal Volume
69
Journal Issue
14
Pages
2971-2976
Date Issued
2013
Author(s)
Abstract
A 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.
Subjects
Annonaceous acetogenin; Asymmetric synthesis; C2 Symmetry; Cross metathesis; Ring-closing metathesis
SDGs
Other Subjects
1,1' [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 reaction
Type
journal article