Stereo selective synthesis of C3-C12 fragment of iriomoteolide-1a

被引：1

作者：

Sharma, Gangavaram V. M. ^{[1
]}

Rajender, Karnekanti ^{[1
,2
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Prades, India

[2] Govt Polytech, Warangal 506007, Telangana State, India

来源：

JOURNAL OF SAUDI CHEMICAL SOCIETY | 2018年 / 22卷 / 02期

关键词：

Iriomoteolide-1a; Mannich reaction; Sharpless epoxidation; Keck allylation; Cross-metathesis; DINOFLAGELLATE AMPHIDINIUM-SP; OLEFIN METATHESIS; STEREOSELECTIVE-SYNTHESIS; MARINE; MACROLIDES; DINOPHYCEAE; ALLYLATION; ALDEHYDE;

D O I：

10.1016/j.jscs.2016.01.008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent and flexible synthetic route for the synthesis of C3-C12 fragment of iriomoteolide-1a is described. The key steps are: Mannich reaction, Keck asymmetric allylation, Sharpless asymmetric epoxidation and cross-metathesis protocol. (C) 2016 King Saud University. Production and hosting by Elsevier B.V.

引用

页码：165 / 172

页数：8

共 50 条

[31] Synthesis of C3-C 12 fragment of 24-demethylbafilomycin C1 via anti-selective aldol condensation as the key stereocontrol step
Dai, Wei-Min
Feng, Gaofeng
Wu, Jinlong
Sun, Liang
SYNLETT, 2008, (07) : 1013 - 1016
[32] Iriomoteolide-1a and-1b: Structure Elucidation by Integrating NMR Spectroscopic Analysis, Theoretical Calculation, and Total Synthesis
Obana, Tomohiro
Nakajima, Miyu
Nakazato, Kazuki
Nakagawa, Hayato
Murata, Keisuke
Tsuda, Masashi
Fuwa, Haruhiko
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (43) : 29836 - 29846
[33] Total Syntheses of the Proposed Structure of Iriomoteolide-1a,-1b and Synthesis of Three Derivatives for Structural Studies
Ghosh, Arun K.
Yuan, Hao
MARINE DRUGS, 2022, 20 (10)
[34] Asymmetric synthesis of the C1-C31 fragment of Amphidinol 3
Grisin, Aleksandr
Evans, P. Andrew
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[35] A synthesis of the C1-N12 tripeptide fragment of sanglifehrin A
Bänteli, R
Brun, I
Hall, P
Metternich, R
TETRAHEDRON LETTERS, 1999, 40 (11) : 2109 - 2112
[36] Enantioselective Synthesis of the C1-C6 and C7-C23 Fragments of the Proposed Structure of Iriomoteolide 1a
Crimmins, Michael T.
Dechert, Anne-Marie R.
ORGANIC LETTERS, 2012, 14 (09) : 2366 - 2369
[37] Studies on the synthesis of tedanolide. 2. Stereoselective synthesis of a protected C(1)-C(12) fragment
Roush, WR
Newcom, JS
ORGANIC LETTERS, 2002, 4 (26) : 4739 - 4742
[38] Synthesis of the C(1)-C(16) fragment of bryostatins
O'Brien, M
Taylor, NH
Thomas, EJ
TETRAHEDRON LETTERS, 2002, 43 (31) : 5491 - 5494
[39] Concise synthesis of the C-1-C-12 fragment of amphidinolides T1-T5
Clark, J. Stephen
Labre, Flavien
Thomas, Lynne H.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) : 4823 - 4830
[40] Enantioselective Synthesis of the C(1)-C(11) Fragment of Tedanolide C
Geist, Julie G.
Barth, Roland
Roush, William R.
ORGANIC LETTERS, 2013, 15 (01) : 58 - 61

← 1 2 3 4 5 →