The first total synthesis of 15-deoxy-Δ 12,14-prostaglandin J2 and the unambiguous assignment of the C14 stereochemistry

被引：47

作者：

Brummond, KM ^{[1
]}

Sill, PC ^{[1
]}

Chen, HF ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 02期

关键词：

D O I：

10.1021/ol035590v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first total synthesis of 15-deoxy-Delta(12,14)-prostaglandin J(2) is reported. The highly unsaturated cyclopentenone prostaglandin was obtained via a silicon-tethered allenic [2 + 2 + 1] cycloaddition reaction developed in our group. In addition, the stereochemistry at C-14 has been assigned unambiguously.

引用

页码：149 / 152

页数：4

共 36 条

[1] PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES
AHMAR, M
ANTRAS, F
CAZES, B
[J]. TETRAHEDRON LETTERS, 1995, 36 (25) : 4417 - 4420
[2] Pauson-Khand reaction with allenic compounds .2. Reactivity of functionalized allenes.
Ahmar, M
Chabanis, O
Gauthier, J
Cazes, B
[J]. TETRAHEDRON LETTERS, 1997, 38 (30) : 5277 - 5280
[3] Pauson-Khand cycloaddition of alpha,omega-allenynes.
Ahmar, M
Locatelli, C
Colombier, D
Cazes, B
[J]. TETRAHEDRON LETTERS, 1997, 38 (30) : 5281 - 5284
[4] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .19. BETA-METHYLENECYCLOPENTENONES VIA IRON CARBONYL-INDUCED [2 + 2 + 1] CYCLOADDITION OF ALKYNES TO ALLENES AND CARBON-MONOXIDE
AUMANN, R
WEIDENHAUPT, HJ
[J]. CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (01): : 23 - 27
[5] A silicon-tethered allenic Pauson-Khand reaction
Brummond, KM
Sill, PC
Rickards, B
Geib, SJ
[J]. TETRAHEDRON LETTERS, 2002, 43 (20) : 3735 - 3738
[6] An intramolecular allenic [2+2+1]cycloaddition
Brummond, KM
Wan, HH
Kent, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) : 6535 - 6545
[7] A short synthesis of the potent antitumor agent (±)-hydroxymethylacylfulvene using an allenic Pauson-Khand type cycloaddition
Brummond, KM
Lu, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5087 - 5088
[8] A rapid synthesis of hydroxymethylacylfulvene (HMAF) using the allenic Pauson-Khand reaction. A synthetic approach to either enantiomer of this illudane structure
Brummond, KM
Lu, JL
Petersen, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) : 4915 - 4920
[9] Brummond KM, 1999, ADV CYCLOAD, V6, P211
[10] SYNTHESIS AND PLATELET-AGGREGATION INHIBITING ACTIVITY OF PROSTAGLANDIN-D ANALOGS
BUNDY, GL
MORTON, DR
PETERSON, DC
NISHIZAWA, EE
MILLER, WL
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) : 790 - 799

← 1 2 3 4 →