TREMORGENIC INDOLE ALKALOIDS .9. ASYMMETRIC CONSTRUCTION OF AN ADVANCED F-G-H-RING LACTONE PRECURSOR FOR THE SYNTHESIS OF PENITREM-D

被引：35

作者：

SMITH, AB ^{[1
]}

NOLEN, EG ^{[1
]}

SHIRAI, R ^{[1
]}

BLASE, FR ^{[1
]}

OHTA, M ^{[1
]}

CHIDA, N ^{[1
]}

HARTZ, RA ^{[1
]}

FITCH, DM ^{[1
]}

CLARK, WM ^{[1
]}

SPRENGELER, PA ^{[1
]}

机构：

[1] UNIV PENN, MONELL CHEM SENSES CTR, PHILADELPHIA, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 24期

关键词：

D O I：

10.1021/jo00129a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lactone (+)-12 is envisioned as the precursor to the F-G-H rings of penitrem D (4) in our ongoing synthetic venture. The efficient, stereocontrolled introduction of the vicinal quaternary methyl groups present the major challenge in the construction of this subunit. Our first route to (+/-)-12 was marked by low overall yield (<2%) and the instability of several key intermediates; these deficiencies were rectified in a second-generation approach that produced optically active material (18 steps from 19a, 2.1% overall). The successful strategies exploited enolate generation via either conjugate additions to alpha,beta-enones or the Evans oxy-Cope rearrangement as key regiochemical control elements.

引用

页码：7837 / 7848

页数：12

共 3 条

[1] AN END-GAME STRATEGY FOR CONSTRUCTION OF THE G-H-I RINGS OF PENITREM-D, A TREMORGENIC INDOLE ALKALOID
SMITH, AB
OHTA, M
CLARK, WM
LEAHY, JW
[J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3033 - 3036
[2] TREMORGENIC INDOLE ALKALOID STUDIES .6. PREPARATION OF AN ADVANCED INTERMEDIATE FOR THE SYNTHESIS OF PENITREM-D - SYNTHESIS OF AN INDOLE-OXOCANE
SMITH, AB
HASELTINE, JN
VISNICK, M
[J]. TETRAHEDRON, 1989, 45 (08) : 2431 - 2449
[3] Synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)trione, the B,C,D ring core of the shermilamine alkaloids
Townsend, NO
Jackson, YA
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) : 3557 - 3563

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