Total synthesis of natural (+)-lasonolide A

被引:37
作者
Kang, SH [1 ]
Kang, SY [1 ]
Kim, CM [1 ]
Choi, HW [1 ]
Jun, HS [1 ]
Lee, BM [1 ]
Park, CM [1 ]
Jeong, JW [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Sch Mol Sci, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
关键词
allylation; macrolides; natural products; olefination; total synthesis;
D O I
10.1002/anie.200352016
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The diastereoselective differentiation of two methylene groups of a cyclic acetal is a unique feature of a highly enantioselective total synthesis of natural (+)-Iasonolide A (see picture), which is used to create the C22 quaternary asymmetric center. Other key strategies are the use of a sulfone-sulfide as a three-carbon fragment with two latent trans double bonds and macrocyclization through an intramolecular Horner-Emmons reaction.
引用
收藏
页码:4779 / 4782
页数:4
相关论文
共 21 条
[1]  
BAUDIN JB, 1993, B SOC CHIM FR, V130, P856
[2]  
Beck H, 1999, EUR J ORG CHEM, V1999, P2991
[3]  
Blakemore PR, 1998, SYNLETT, P26
[5]  
FLEMING I, 1981, J CHEM SOC P1, P25
[6]  
GASH VW, 1972, J ORG CHEM, V37, P2197, DOI 10.1021/jo00978a029
[7]   Stereocontrolled synthesis of spirocyclopropane sugars and their application to asymmetric formation of tertiary chiral centres: A route to 2,2'-dialkylated pyranose subunit (C-18-C-23) of lasonolide A [J].
Gurjar, MK ;
Kumar, P ;
Rao, BV .
TETRAHEDRON LETTERS, 1996, 37 (47) :8617-8620
[8]   Preparation of 4,5-cyclopropylsugar derivatives: Application to the stereocontrolled synthesis of bottom half (C-7-C-16) segment of lasonolide A [J].
Gurjar, MK ;
Chakrabarti, A ;
Rao, BV ;
Kumar, P .
TETRAHEDRON LETTERS, 1997, 38 (39) :6885-6888
[9]   LASONOLIDE-A, A NEW CYTOTOXIC MACROLIDE FROM THE MARINE SPONGE FORCEPIA SP [J].
HORTON, PA ;
KOEHN, FE ;
LONGLEY, RE ;
MCCONNELL, OJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6015-6016
[10]   CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].
JADHAV, PK ;
BHAT, KS ;
PERUMAL, PT ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439