Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction

被引：9

作者：

Urosa, Aitor ^{[1
]}

Marcos, Isidro S. ^{[1
]}

Diez, David ^{[1
]}

Padron, Jose M. ^{[2
]}

Basabe, Pilar ^{[1
]}

机构：

[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, E-37008 Salamanca, Spain

[2] Univ La Laguna, Ctr Invest Biomed Canarias CIBICAN, Inst Univ Bioorgan Antonio Gonzalez IUBO AG, BioLab, San Cristobal la Laguna 38206, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 12期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; MARINE SPONGE; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; SESTERTERPENOLIDES; DYSIDIOLIDE; INHIBITOR; ANALOGS; ACID;

D O I：

10.1021/acs.joc.5b00876

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of luffarin L (1) and 16-epi-luffarin L (2) by a silicon-tethered ring closing metathesis as a key step has been achieved. The stereochemistry and absolute configuration of the natural sesterterpenolide luffarin L (1) and a new route for the stereoselective synthesis of sesterterpenolides with a luffarane skeleton have been established.

引用

页码：6447 / 6455

页数：9

共 6 条

[1] Ring-closing metathesis as key step in the synthesis of Luffarin I, 16-epi-Luffarin I and Luffarin A
Urosa, Aitor
Marcos, Isidro S.
Diez, David
Plata, Gabriela B.
Padron, Jose M.
Basabe, Pilar
MOLECULAR DIVERSITY, 2016, 20 (02) : 369 - 377
[2] Temporary Silicon-Tethered Ring-Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis
Cusak, Alen
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) : 5800 - 5824
[3] Medium-Ring Stereocontrol in the Temporary Silicon-Tethered Ring-Closing Metathesis Approach to the Synthesis of Polyketide Fragments
Evans, P. Andrew
Cusak, Alen
Grisin, Aleksandr
Lawler, Michael J.
Pink, Maren
SYNTHESIS-STUTTGART, 2016, 48 (15): : 2402 - 2412
[4] Total Synthesis of Umuravumbolide and Hyptolide Through Silicon-Tethered Ring-Closing Metathesis
Chowdhury, Partha Sarathi
Kumar, Pradeep
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (21) : 4586 - 4593
[5] Total synthesis of (+)-pericosine B and (+)-pericosine C and their enantiomers by using the Baylis-Hillman reaction and ring-closing metathesis as key steps
Reddy, Y. Suman
Kadigachalam, P.
Basak, Ranjan K.
Pal, A. P. John
Vankar, Yashwant D.
TETRAHEDRON LETTERS, 2012, 53 (02) : 132 - 136
[6] Synthesis of 4a-carba-β-L-lyxofuranose, 4a-carba-β-L-arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis
Mishra, Girija Prasad
Kumar, Bejugam Santhosh
Rao, B. Venkateswara
TETRAHEDRON-ASYMMETRY, 2012, 23 (15-16) : 1161 - 1169

← 1 →