Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin

被引:29
作者
Zhao, Hongda
Gorman, Jeffrey S. T.
Pagenkopf, Brian L. [1 ]
机构
[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada
[2] Univ Texas, Dept Chem, Austin, TX 78712 USA
关键词
D O I
10.1021/ol061847o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lewis acids control regioselectivity in the alkylation of epi-chlorohydrin and the stereochemistry of an alkyne addition to set the C24/C23 anti relationship. These advances facilitate an efficient total synthesis of bullatacin in 13.3% overall yield from commercial starting materials.
引用
收藏
页码:4379 / 4382
页数:4
相关论文
共 36 条
[1]   Dynamic function of the alkyl spacer of acetogenins in their inhibitory action with mitochondrial complex I (NADH-ubiquinone oxidoreductase) [J].
Abe, M ;
Murai, M ;
Ichimaru, N ;
Kenmochi, A ;
Yoshida, T ;
Kubo, A ;
Kimura, Y ;
Moroda, A ;
Makabe, H ;
Nishioka, T ;
Miyoshi, H .
BIOCHEMISTRY, 2005, 44 (45) :14898-14906
[2]   Annonaceous acetogenins: Recent progress [J].
Alali, FQ ;
Liu, XX ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540
[3]   SYNTHESIS OF POLYCYCLIC POLYETHERS .1. STEREOSELECTIVITY OF THE HETEROCYCLIZATION OF GAMMA-DELTA-ETHYLENE TETRAHYDROFURFURYLIC ALCOHOLS WITH MERCURIC-SALTS [J].
AMOUROUX, R ;
CHASTRETTE, F ;
CHASTRETTE, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :565-569
[4]   Total synthesis of asimicin and bullatacin [J].
Avedissian, H ;
Sinha, SC ;
Yazbak, A ;
Sinha, A ;
Neogi, P ;
Sinha, SC ;
Keinan, E .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6035-6051
[5]   Acetogenins from Annonaceae:: recent progress in isolation, synthesis and mechanisms of action [J].
Bermejo, A ;
Figadère, B ;
Zafra-Polo, MC ;
Barrachina, I ;
Estornell, E ;
Cortes, D .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :269-303
[6]   Enantioselective total synthesis of (+)-rogioloxepane A [J].
Crimmins, MT ;
DeBaillie, AC .
ORGANIC LETTERS, 2003, 5 (17) :3009-3011
[7]  
Emde U, 2000, EUR J ORG CHEM, V2000, P1889
[8]   Enantioselective synthesis of the 4-hydroxy buteneolide terminus of mucocin and related annonaceous acetogenins [J].
Evans, PA ;
Murthy, VS .
TETRAHEDRON LETTERS, 1998, 39 (52) :9627-9628
[9]   Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246
[10]   STEREOCHEMISTRY OF MONO-TETRAHYDROFURANYL MOIETY IN CYTOTOXIC POLYKETIDES .A. SYNTHESIS OF MODEL COMPOUNDS [J].
GALE, JB ;
YU, JG ;
HU, XFE ;
KHARE, A ;
HO, DK ;
CASSADY, JM .
TETRAHEDRON LETTERS, 1993, 34 (37) :5847-5850