FORMAL TOTAL SYNTHESIS OF ENANTIOPURE TRICYCLIC (S)-MYRMICARIN ALKALOIDS 217, 215A AND 215B

被引：5

作者：

Santarem, Marco ^{[1
]}

Vanucci-Bacque, Corinne ^{[1
]}

Lhommet, Gerard ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, IPCM, UMR 7201, F-75252 Paris, France

来源：

HETEROCYCLES | 2010年 / 81卷 / 11期

关键词：

Alkaloid; Myrmicarin; Aldol Reaction; Pyrrolidine; Pyrrole;

D O I：

10.3987/COM-10-12010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We described herein a formal synthesis of the enantiopure tricyclic (4aS)-myrmicarin alkaloids 217, 215A and 215B owing to the obtention of a common pyrroloindolizidine intermediate, starting from a chiral cis-(2S,5R)-disubstitated pyrrolidine. An intramolecular one-pot aldolization-crotonization-aromatization process of a diketo indolizidine constitutes the key step for the formation of the pyrrole ring of the target compound.

引用

页码：2523 / 2537

页数：15

共 15 条

[1] Reversible Dimerization of (+)-Myrmicarin 215B
Ondrus, Alison E.
Movassaghi, Mohammad
ORGANIC LETTERS, 2009, 11 (14) : 2960 - 2963
[2] General synthesis of pyrroloquinolizidines: Synthesis of an unnatural homologue of the pyrroloindolizidine myrmicarin alkaloid 215B
Angle, Steven R.
Qian, Xuelei Lily
Pletnev, Alexandre A.
Chinn, Jason
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06): : 2015 - 2020
[3] Dimerization of (+)-myrmicarin 215B. A potential biomimetic approach to complex myrmicarin alkaloids
Ondrus, Alison E.
Movassaghi, Mohammad
TETRAHEDRON, 2006, 62 (22) : 5287 - 5297
[4] Enantioselective total synthesis of tricyclic myrmicarin alkaloids
Movassaghi, M
Ondrus, AE
ORGANIC LETTERS, 2005, 7 (20) : 4423 - 4426
[5] An approach to total synthesis of the cylindricine B pyridoquinoline subclass of tricyclic marine ascidian alkaloids
Chao, Wenchun
Mahajan, Yogesh R.
Weinreb, Steven M.
TETRAHEDRON LETTERS, 2006, 47 (23) : 3815 - 3818
[6] Intramolecular cyclodehydration of (4S)-(+)-4-carboxyethyl-4-(pyrrol-1-yl)butanal as the key step in the formal synthesis of (S)-(-)-Myrmicarin 217
Settambolo, R
Guazzelli, G
Lazzaroni, R
TETRAHEDRON-ASYMMETRY, 2003, 14 (11) : 1447 - 1449
[7] Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B
Angle, SR
Henry, RM
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24): : 8549 - 8552
[8] Progress toward the total synthesis of Alstonia indole alkaloids peraksine and macrosalhine bromide as well as the formal total synthesis of secotalcarpine and macrocarpine B
Edwankar, Rahul V.
Edwankar, Chitra R.
Cook, James M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[9] Enantiocontrolled formal total synthesis of paeonilactone A and B from (S)-(+)-carvone
Ronn, M
Andersson, PG
Backvall, JE
ACTA CHEMICA SCANDINAVICA, 1998, 52 (05): : 524 - 527
[10] Total Synthesis of Indolizidine Alkaloids (-)-167B, (-)-209I, and (-)-223A by Using a Common Tricyclic Lactone
Li, Yu-Jang
Hou, Chung-Chien
Chang, Kuei-Chen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) : 1659 - 1663

← 1 2 →