An enantioselective synthesis of cryptocarya diacetate

被引:65
作者
Hunter, TJ [1 ]
O'Doherty, GA [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol016399t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The enantioselective synthesis of cryptocarya diacetate has been achieved in 10 steps from ethyl sorbate. The route relies upon an enantio-and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a delta -hydroxy-1-enoate, which was subsequently converted into a benzylidene-protected 3,5-dihydroxy carboxylic ester. This ester was converted into cryptocarya diacetate in 14% overall yield via an allylation and methathesis ring closure reaction sequence.
引用
收藏
页码:2777 / 2780
页数:4
相关论文
共 28 条
[1]   Two 6-substituted 5,6-dihydro-α-pyrones from Ravensara anisata [J].
Andrianaivoravelona, JO ;
Sahpaz, S ;
Terreaux, C ;
Hostettmann, K ;
Stoeckli-Evans, H ;
Rasolondramanitra, J .
PHYTOCHEMISTRY, 1999, 52 (02) :265-269
[2]   Total synthesis of fostriecin (CI-920) [J].
Boger, DL ;
Ichikawa, S ;
Zhong, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167
[3]   Absolute configuration of alpha-pyrones from Cryptocarya latifolia and Syncolostemon densiflorus [J].
Collett, LA ;
DaviesColeman, MT ;
Rivett, DEA ;
Drewes, SE ;
Horn, MM .
PHYTOCHEMISTRY, 1997, 44 (05) :935-938
[4]   Synthesis of the C1-C12 fragment of fostriecin [J].
Cossy, J ;
Pradaux, F ;
BouzBouz, S .
ORGANIC LETTERS, 2001, 3 (14) :2233-2235
[5]   5,6-DIHYDRO-ALPHA-PYRONES AND 2 BICYCLIC TETRAHYDRO-ALPHA-PYRONE DERIVATIVES FROM CRYPTOCARYA-LATIFOLIA [J].
DREWES, SE ;
SEHLAPELO, BM ;
HORN, MM ;
SCOTTSHAW, R ;
SANDOR, P .
PHYTOCHEMISTRY, 1995, 38 (06) :1427-1430
[6]   Passifloricins, polyketides α-pyrones from Passiflora foetida resin [J].
Echeverri, F ;
Arango, V ;
Quiñones, W ;
Torres, F ;
Escobar, G ;
Rosero, Y ;
Archbold, R .
PHYTOCHEMISTRY, 2001, 56 (08) :881-885
[7]   DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES [J].
EVANS, DA ;
GAUCHETPRUNET, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2446-2453
[8]   Enantioselective total synthesis of altohyrtin C (spongistatin 2) [J].
Evans, DA ;
Trotter, BW ;
Coleman, PJ ;
Côté, B ;
Dias, LC ;
Rajapakse, HA ;
Tyler, AN .
TETRAHEDRON, 1999, 55 (29) :8671-8726
[9]   A stereoselective synthesis of (+)-boronolide [J].
Ghosh, AK ;
Bilcer, G .
TETRAHEDRON LETTERS, 2000, 41 (07) :1003-1006
[10]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450