Chemoenzymatic approaches to the montanine alkaloids: A total synthesis of (+)-brunsvigine

被引:56
作者
Banwell, Martin G. [1 ]
Kokas, Okanya J. [1 ]
Willis, Anthony C. [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
D O I
10.1021/ol071344y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The readily available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1].
引用
收藏
页码:3503 / 3506
页数:4
相关论文
共 28 条
[1]   Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors [J].
Banwell, MG ;
Edwards, AJ ;
Harfoot, GJ ;
Jolliffe, KA ;
McLeod, MD ;
McRae, KJ ;
Stewart, SG ;
Vögtle, M .
PURE AND APPLIED CHEMISTRY, 2003, 75 (2-3) :223-229
[2]   Selective cleavage of N-benzyl-protected secondary amines by triphosgene [J].
Banwell, MG ;
Coster, MJ ;
Harvey, MJ ;
Moraes, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :613-616
[3]  
Banwell MG, 2001, J CHEM SOC PERK T 1, P2194, DOI 10.1039/b105376k
[4]   An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine [J].
Banwell, MG ;
Edwards, AJ ;
Jolliffe, KA ;
Kemmler, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (12) :1345-1348
[5]  
BUCKINGHAM J, 1994, DICTIONARY NATURAL P, V4, P4432
[6]   ALKALOIDS OF AMARYLLIDACEAE - BRUNSVIGINE - NMR, ORD-CD AND MASS-SPECTROMETRY, DEGRADATION AND INTERCONVERSION STUDIES [J].
CLARK, RC ;
WARREN, FL ;
PACHLER, KGR .
TETRAHEDRON, 1975, 31 (16) :1855-1859
[7]   THE ALKALOIDS OF THE AMARYLLIDACEAE .4. THE ALKALOIDS OF BRUNSVIGIA COOPERI BAKER [J].
DRY, LJ ;
POYNTON, M ;
THOMPSON, ME ;
WARREN, FL .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (DEC) :4701-4704
[8]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .2. [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2866-2869
[9]  
Hoshino O., 1998, The Alkaloids: Chemistry and Biology, P323
[10]  
Hudlicky T, 1999, ALDRICHIM ACTA, V32, P35