Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin

被引:52
作者
Hayes, Christopher J. [1 ]
Sherlock, Alexandra E. [1 ]
Green, Martin P. [1 ]
Wilson, Claire [1 ]
Blake, Alexander J. [1 ]
Selby, Matthew D. [2 ]
Prodger, Jeremy C. [3 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England
[3] GlaxoSmithKline Inc, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/jo7027695
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.
引用
收藏
页码:2041 / 2051
页数:11
相关论文
共 83 条
[1]  
ADAM G, 1988, SYNTHESIS-STUTTGART, P373
[2]   Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions [J].
Adinolfi, M ;
Barone, G ;
Guariniello, L ;
Iadonisi, A .
TETRAHEDRON LETTERS, 1999, 40 (48) :8439-8441
[3]   Transformations of cyclic acetals under the action of some organic and inorganic oxidants [J].
Akbalina, ZF ;
Zlotskii, SS ;
Kabal'nova, NN ;
Grigor'ev, IA ;
Kotlyar, SA ;
Shereshovets, VV .
RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2002, 75 (07) :1120-1122
[4]   An enantioselective formal total synthesis of (-)-TAN1251A [J].
Auty, JMA ;
Churcher, I ;
Hayes, CJ .
SYNLETT, 2004, (08) :1443-1445
[5]   TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].
BAKER, R ;
CASTRO, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :47-65
[6]   α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].
Balskus, Emily P. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812
[7]   REGIOSELECTIVE RING-OPENING OF SELECTED BENZYLIDENE ACETALS - A PHOTOCHEMICALLY INITIATED REACTION FOR PARTIAL DEPROTECTION OF CARBOHYDRATES [J].
BINKLEY, RW ;
GOEWEY, GS ;
JOHNSTON, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (06) :992-996
[8]   Formal synthesis of (+)-lactacystin based on a novel radical cyclisation of an α-ethynyl substituted serine [J].
Brennan, CJ ;
Pattenden, G ;
Rescourio, G .
TETRAHEDRON LETTERS, 2003, 44 (49) :8757-8760
[9]  
CALDWELL CG, 1990, SYNTHESIS-STUTTGART, P34
[10]   META-CHLOROPEROXYBENZOIC ACID POTASSIUM FLUORIDE SYSTEM - STUDY OF ITS STABILITY AND REACTION WITH ALPHA-METHYLSTYRENE [J].
CAMPS, F ;
COLL, J ;
MESSEGUER, A ;
PUJOL, F .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5402-5404