A biomimetic approach to the synthesis of an antiviral marine steroidal orthoester

被引：20

作者：

Giner, JL ^{[1
]}

Faraldos, JA ^{[1
]}

机构：

[1] SUNY ESF, Dept Chem, Syracuse, NY 13210 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 08期

关键词：

D O I：

10.1021/jo011111z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Orthoesterol B, a marine natural product exhibiting antiviral activities, contains a [3.2.1]-bicyclic orthobutyrate bridging the steroid side chain and ring D. A biosynthetic reaction was proposed by which rearrangement of an epoxy ester results in the formation of the orthoester moiety. Steroidal model compounds incorporating 16-butyroxy and 20,22-epoxy groups were synthesized from tigogenin and were shown to rearrange to orthoesters under mild acidic catalysis.

引用

收藏

页码：2717 / 2720

页数：4

相关论文

共 16 条

[1]

Baldwin JE, 1998, ANGEW CHEM INT EDIT, V37, P2661, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2661::AID-ANIE2661>3.0.CO

[2]

2-D

[3]

Baldwin JE, 1999, CHEM-EUR J, V5, P3154, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3154::AID-CHEM3154>3.0.CO

[4]

2-7

[5] 2,3-OXIDOSQUALENE AN INTERMEDIATE IN BIOLOGICAL SYNTHESIS OF STEROLS FROM SQUALENE [J].

COREY, EJ ;

RUSSEY, WE ;

DEMONTEL.PR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (20) :4750-&

[6] PETUNIASTERONES, NOVEL ERGOSTANE-TYPE STEROIDS OF PETUNIA-HYBRIDIA VILM (SOLANACEAE) HAVING INSECT-INHIBITORY ACTIVITY - X-RAY MOLECULAR-STRUCTURE OF THE 22,24,25-[(METHOXYCARBONYL)ORTHOACETATE] OF 7-ALPHA,22,24,25-TETRAHYDROXY ERGOSTA-1,4-DIEN-3-ONE AND OF 1-ALPHA-ACETOXY-24,25-EPOXY-7-ALPHA-HYDROXY-22-(METHYLTHIOCARBONYL)ACETOXYERGOST-4-EN-3-ONE [J].

ELLIGER, CA ;

BENSON, ME ;

HADDON, WF ;

LUNDIN, RE ;

WAISS, AC ;

WONG, RY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :711-717

[7] Sterols of the marine sponge Petrosia weinbergi:: implications for the absolute configurations of the antiviral orthoesterols and weinbersterols [J].

Giner, JL ;

Gunasekera, SP ;

Pomponi, SA .

STEROIDS, 1999, 64 (12) :820-824

[8] ACETYLENIC BOND PARTICIPATION IN BIOMIMETIC POLYENE CYCLIZATIONS - MODEL STUDIES DIRECTED TOWARD SYNTHESIS OF 20-KETO STEROIDS - SYNTHESIS OF DL-PROGESTERONE AND DL-DELTA-4-ANDROSTENE-3,17-DIONE [J].

GRAVESTOCK, MB ;

JOHNSON, WS ;

MCCARRY, BE ;

PARRY, RJ ;

RATCLIFFE, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4274-4282

[9] Nature knows best: An amazing reaction cascade is uncovered by design and discovery [J].

Heathcock, CH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (25) :14323-14327

[10]

HERGENHAHN M, 1975, TETRAHEDRON LETT, P1595