Total syntheses of (±)-preussomerins G and I

被引：40

作者：

Chi, S ^{[1
]}

Heathcock, CH ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 01期

关键词：

D O I：

10.1021/ol990020+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.

引用

页码：3 / 5

页数：3

共 31 条

[1] Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371:: novel spiro-ketal fungal metabolites
Barrett, AGM
Hamprecht, D
Meyer, T
[J]. CHEMICAL COMMUNICATIONS, 1998, (07) : 809 - 810
[2] SCH-50673 AND SCH-50676, 2 NOVEL ANTITUMOR FUNGAL METABOLITES
CHU, M
TRUUMEES, I
PATEL, M
BLOOD, C
DAS, PR
PUAR, MS
[J]. JOURNAL OF ANTIBIOTICS, 1995, 48 (04) : 329 - 331
[3] STRUCTURE OF SCH-49209 - A NOVEL ANTITUMOR AGENT FROM THE FUNGUS NATTRASSIA-MANGIFERAE
CHU, M
TRUUMEES, I
PATEL, MG
GULLO, VP
PUAR, MS
MCPHAIL, AT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 1222 - 1223
[4] SCH 53823 and SCH 53825, novel fungal metabolites with phospholipase D inhibitory activity
Chu, M
Patel, MG
Pai, JK
Das, PR
Puar, MS
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (05) : 579 - 584
[5] A NOVEL CLASS OF ANTITUMOR METABOLITES FROM THE FUNGUS NATTRASSIA-MANGIFERAE
CHU, M
TRUUMEES, I
PATEL, MG
GULLO, VP
BLOOD, C
KING, I
PAI, JK
PUAR, MS
[J]. TETRAHEDRON LETTERS, 1994, 35 (09) : 1343 - 1346
[6] COREY E, 1992, TETRAHEDRON LETT, V51, P6735
[7] CONVENIENT SYNTHESIS OF QUINONES FROM HYDROQUINONE DIMETHYL ETHERS - OXIDATIVE DEMETHYLATION WITH CERIC AMMONIUM-NITRATE
JACOB, P
CALLERY, PS
SHULGIN, AT
CASTAGNOLI, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) : 3627 - 3629
[8] Biologically active metabolites from fungi .9. New palmarumycins CP4a, and CP5 from Coniothyrium palmarum: Structure elucidation, crystal structure analysis and determination of the absolute configuration by CD calculations
Krohn, K
Beckmann, K
Florke, U
Aust, HJ
Draeger, S
Schulz, B
Busemann, S
Bringmann, G
[J]. TETRAHEDRON, 1997, 53 (09) : 3101 - 3110
[9] Krohn K, 1997, LIEBIGS ANN-RECL, P2531
[10] KROHN K, 1994, LIEBIGS ANN CHEM, P1099

← 1 2 3 4 →