SYNTHESIS OF THE NAPHTHOQUINONE NUCLEUS OF AWAMYCIN

被引：16

作者：

ROUSH, WR

COFFEY, DS

机构：

[1] Department of Chemistry, Indiana University, Bloomington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 14期

关键词：

D O I：

10.1021/jo00119a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

引用

页码：4412 / 4418

页数：7

共 50 条

[1] TOTAL SYNTHESIS OF (+)-MACBECIN-I
BAKER, R
CASTRO, JL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01): : 47 - 65
[2] REGIOSPECIFIC ALPHA-SUBSTITUTION OF CROTONIC ESTERS - SYNTHESIS OF NATURALLY-OCCURRING 3-O-METHYLRUBIADINS
CARON, B
BRASSARD, P
[J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04): : 1123 - 1126
[3] AN EFFICIENT SYNTHESIS OF THE NAPHTHALENE SUBUNITS OF THE PROTEIN-KINASE-C INHIBITOR CALPHOSTIN-C
COLEMAN, RS
GRANT, EB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) : 1357 - 1359
[4] SYNTHESIS OF ANTITUMOR ANSAMYCINS .2. A FORMAL SYNTHESIS OF (+/-)-MACBECIN-I
COUTTS, SJ
KALLMERTEN, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (30) : 4305 - 4308
[5] CRICCHIO P, 1980, J ANTIBIOT, V33, P842
[6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[7] TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC CP-61,405 (ROUTIENNOCIN)
DIEZMARTIN, D
KOTECHA, NR
LEY, SV
MANTEGANI, S
MENENDEZ, JC
ORGAN, HM
WHITE, AD
BANKS, BJ
[J]. TETRAHEDRON, 1992, 48 (37) : 7899 - 7938
[8] ASYMMETRIC-SYNTHESIS OF THE BENZOQUINOID ANSAMYCIN ANTITUMOR ANTIBIOTICS - TOTAL SYNTHESIS OF (+)-MACBECIN
EVANS, DA
MILLER, SJ
ENNIS, MD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 471 - 485
[9] FRASERREID B, 1987, J ORG CHEM, V52, P4505, DOI 10.1021/jo00229a014
[10] DIPYRANOSIDE PRECURSORS FOR ANSAMYCINS - PYRANOSIDIC HOMOLOGATION .5.
FRASERREID, B
MAGDZINSKI, L
MOLINO, BF
MOOTOO, DR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) : 4495 - 4504

← 1 2 3 4 5 →