Ring-closing metathesis as key step in the synthesis of Luffarin I, 16-epi-Luffarin I and Luffarin A

被引：5

作者：

Urosa, Aitor ^{[1
]}

Marcos, Isidro S. ^{[1
]}

Diez, David ^{[1
]}

Plata, Gabriela B. ^{[2
]}

Padron, Jose M. ^{[2
]}

Basabe, Pilar ^{[1
]}

机构：

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

[2] Univ La Laguna, BioLab, Ctr Invest Biomed Canarias CIBICAN, Inst Univ Bioorgan Antonio Gonzalez, E-38207 San Cristobal la Laguna, Spain

来源：

MOLECULAR DIVERSITY | 2016年 / 20卷 / 02期

关键词：

Ring-closing metathesis; Marine natural products; Luffarins; Yamaguchi esterefication; Cancer; Faulkner oxidation; MARINE SPONGE; SESTERTERPENES; LACTONES;

D O I：

10.1007/s11030-015-9638-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Natural sesterterpenolides, luffarin I and luffarin A, from Luffariella geometrica have been synthesized, and this is the first reported synthesis of luffarin A. The Yamaguchi esterification of the nor-diterpenic fragment, obtained from 2.8-15 M, with the appropriate furane alcohols yielded the necessary diene intermediates for the synthesis of the target molecules. The key strategic step in this synthesis was the ring-closing metathesis (RCM) reaction of the diene intermediates. This strategy allowed for the synthesis of 16-epi-luffarin I and analogues for structure-activity relationship (SAR) studies. The most active compound exhibited antiproliferative activity against a panel of six human solid tumour cell lines with values in the range 2.8-15 M.

引用

页码：369 / 377

页数：9

共 18 条

[1] Ring-closing metathesis as key step in the synthesis of Luffarin I, 16-epi-Luffarin I and Luffarin A
Aitor Urosa
Isidro S. Marcos
David Díez
Gabriela B. Plata
José M. Padrón
Pilar Basabe
Molecular Diversity, 2016, 20 : 369 - 377
[2] Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction
Urosa, Aitor
Marcos, Isidro S.
Diez, David
Padron, Jose M.
Basabe, Pilar
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12) : 6447 - 6455
[3] Synthesis and Bioactivity of Luffarin I
Urosa, Aitor
Marcos, Isidro S.
Diez, David
Lithgow, Anna
Plata, Gabriela B.
Padron, Jose M.
Basabe, Pilar
MARINE DRUGS, 2015, 13 (04): : 2407 - 2423
[4] Ring-closing metathesis as a key step in the synthesis of 2-pyridones and pyridine triflates
Donohoe, Timothy J.
Fishlock, Lisa P.
Procopiou, Panayiotis A.
SYNTHESIS-STUTTGART, 2008, (16): : 2665 - 2667
[5] A domino ring-closing metathesis as a key-step in the synthesis of chiral lactones from D-mannitol
Nay, B
Gaboriaud-Kolar, N
Bodo, B
TETRAHEDRON LETTERS, 2005, 46 (22) : 3867 - 3870
[6] Synthesis of catenanes and molecular knots by copper(I)-directed formation of the precursors followed by ruthenium(II)-catalysed ring-closing metathesis
Dietrich-Buchecker, C
Rapenne, G
Sauvage, JP
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 : 167 - 176
[7] Ring-closing metathesis as a key step to construct the 2,6-dihydropyrano[2,3-c]pyrazole ring system
Bieliauskas, Aurimas
Krikstolaityte, Sonata
Holzer, Wolfgang
Sackus, Algirdas
ARKIVOC, 2018, : 296 - 307
[8] Ring-Closing Metathesis of (η5- Alkenylcyclopentadienyl)( alkenyl-phosphine) manganese(I) Dicarbonyl Complexes
Tseng, Ya-Yi
Kamikawa, Ken
Wu, Qian
Takahashi, Tamotsu
Ogasawara, Masamichi
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2255 - 2264
[9] Synthesis of Two Diastereomers of Iriomoteolide-1a via a Tunable Four-Module Coupling Approach Using Ring-Closing Metathesis as the Key Step
Liu, Yuanxin
Feng, Gaofeng
Wang, Jian
Wu, Jinlong
Dai, Wei-Min
SYNLETT, 2011, (12) : 1774 - 1778
[10] Origin of the selectivity in the ring-closing metathesis step of the synthesis of (-)-callyspongiolide: Formation of fourteen-versus eight-membered rings
Diaz-Ruiz, Marina
Urbina, Aina
Llor, Nuria
Bosch, Joan
Amat, Mercedes
Maseras, Feliu
TETRAHEDRON, 2022, 124

← 1 2 →