Studies toward the total synthesis of Cytospolide E

被引：9

作者：

Vadhadiya, Paresh M. ^{[1
]}

Rout, Jeetendra K. ^{[1
]}

Ramana, C. V. ^{[1
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2015年 / 71卷 / 48期

关键词：

Nonenolide; Yamaguchi esterification; Ring closing metathesis; Shiina lactonization; 20-Membered macrodiolide; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; VERSATILE INTERMEDIATE; MIXED ANHYDRIDE; LACTONES; (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE; ELEUTHEROBIN; DERIVATIVES;

D O I：

10.1016/j.tet.2015.10.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this manuscript, we describe various approaches that we have examined towards the total synthesis of Cytospolide E. We initially attempted the RCM approach employing first and second generation Grubbs and Grubbs-Hoyeda catalysts resulting in the exclusive synthesis of the Z-isomer of Cytospolide E. With the Furstner catalyst, the dimerization involving the less hindered olefin was the exclusive event. Alternative approach documented is a successful cross-metathesis leading to a seco-acid with the requisite E-configuration and undesired macrodiolide formation during the attempted Shiina's lactonization. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：9088 / 9094

页数：7

共 33 条

[1] ACKER RD, 1977, TETRAHEDRON LETT, P3407
[2] Effects of allylic and homoallylic substituents on the ring closing metathesis reaction used to synthesise simplified eleuthesides
Caggiano, L
Castoldi, D
Beumer, R
Bayón, P
Tesler, J
Gennari, C
[J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 7913 - 7919
[3] A formal total synthesis of eleutherobin using the ring-closing metathesis (RCM) reaction of a densely functionalized diene as the key step: Investigation of the unusual kinetically controlled RCM stereochemistry
Castoldi, D
Caggiano, L
Panigada, L
Sharon, O
Costa, AM
Gennari, C
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (01) : 51 - 62
[4] A general model for selectivity in olefin cross metathesis
Chatterjee, AK
Choi, TL
Sanders, DP
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
[5] (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE, A VERSATILE INTERMEDIATE FOR ASYMMETRIC-SYNTHESIS OF CHIRAL ALCOHOL
CHATTOPADHYAY, A
MAMDAPUR, VR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) : 585 - 587
[6] (R)-2,3-O-cyclohexylideneglyceraldehyde, a versatile intermediate for asymmetric synthesis of homoallyl and homopropargyl alcohols in aqueous medium
Chattopadhyay, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6104 - 6107
[7] (R)-2,3-Cyclohexylideneglyceraldehyde:: a novel template for simple entry into both cis- and trans-2,5-disubstituted tetrahydrofurans
Chattopadhyay, Angshuman
Vichare, Prasad
Dhotare, Bhaskar
[J]. TETRAHEDRON LETTERS, 2007, 48 (16) : 2871 - 2873
[8] A stereoselective synthesis of the macrolide core of migrastatin
Das, Parthasarathi
Saibaba, Vobbalareddy
Kumar, Chetlur Kiran
Mahendar, Velisoju
[J]. SYNTHESIS-STUTTGART, 2008, 3 (03): : 445 - 451
[9] A short approach to trisubstituted γ-butyrolactones
Dias, LC
de Castro, IBD
Steil, LJ
Augusto, T
[J]. TETRAHEDRON LETTERS, 2006, 47 (02) : 213 - 216
[10] Synthesis of the Macrolactone of Migrastatin and Analogues with Potent Cell-Migration Inhibitory Activity
Dias, Luiz C.
Finelli, Fernanda G.
Conegero, Leila S.
Krogh, Renata
Andricopulo, Adriano D.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (35) : 6748 - 6759

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