Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A

被引：19

作者：

Caso, Alessia ^{[1
]}

Mangoni, Alfonso ^{[1
]}

Piccialli, Gennaro ^{[1
]}

Costantino, Valeria ^{[1
]}

Piccialli, Vincenzo ^{[2
]}

机构：

[1] Univ Naples Federico II, Dept Pharm, I-80131 Naples, Italy

[2] Univ Naples Federico II, Dept Chem Sci, Via Cintia 4, I-80126 Naples, Italy

来源：

ACS OMEGA | 2017年 / 2卷 / 04期

关键词：

CYANOBACTERIUM LYNGBYA-MAJUSCULA; MARINE CYANOBACTERIUM; CARIBBEAN SPONGE; PERRUTHENATE; MALYNGAMIDES; PTERULONE; UNIT;

D O I：

10.1021/acsomega.7b00095

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral pool protocol toward the synthesis of the smenamide family of natural products is described. Two stereoisomers of smenamide A, namely, ent-smenamide A and 16-epi-smenamide A were synthesized with a 2.6 and 2.5% overall yield, respectively. Their carboxylic acid moieties were assembled starting from S-citronellene via two Wittig reactions and a Grignard process. Its coupling with either (S)-or (R)dolapyrrolidinone, synthesized from Boc-L-Phe and Boc-D-Phe, respectively, was accomplished by using the Andrus protocol. This work also established the previously unknown relative and absolute configurations of smenamide A.

引用

收藏

页码：1477 / 1488

页数：12

相关论文

共 35 条

[1] Synthesis of mixed acyclic imides using pentafluorophenyl esters [J].

Andrus, MB ;

Li, W ;

Keyes, RF .

TETRAHEDRON LETTERS, 1998, 39 (31) :5465-5468

[2] Synthesis of microcolin B, a potent new immunosuppressant using an efficient mixed imide formation reaction [J].

Andrus, MB ;

Li, WK ;

Keyes, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5542-5549

[3] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Keyzers, Robert A. ;

Munro, Murray H. G. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2016, 33 (03) :382-431

[4] Total synthesis of malyngamide M and isomalyngamide M [J].

Chen, Jie ;

Shi, Zi-Fa ;

Zhou, Ling ;

Xie, An-Le ;

Cao, Xiao-Ping .

TETRAHEDRON, 2010, 66 (19) :3499-3507

[5] Total Synthesis, Stereochemical Assignment, and Antimalarial Activity of Gallinamide A [J].

Conroy, Trent ;

Guo, Jin T. ;

Linington, Roger G. ;

Hunt, Nicholas H. ;

Payne, Richard J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) :13544-13552

[6] Corrugoside, a new immunostimulatory α-galactoglycosphingolipid from the marine sponge Axinella corrugata [J].

Costantino, Valeria ;

Fattorusso, Ernesto ;

Imperatore, Concetta ;

Mangoni, Alfonso ;

Freigang, Stefan ;

Teyton, Luc .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (04) :2077-2085

[7] Tedanol: A potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis [J].

Costantino, Valeria ;

Fattorusso, Ernesto ;

Mangoni, Alfonso ;

Perinu, Cristina ;

Cirino, Giuseppe ;

De Gruttola, Luana ;

Roviezzo, Fiorentina .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (21) :7542-7547

[8] Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula [J].

Edwards, DJ ;

Marquez, BL ;

Nogle, LM ;

McPhail, K ;

Goeger, DE ;

Roberts, MA ;

Gerwick, WH .

CHEMISTRY & BIOLOGY, 2004, 11 (06) :817-833

[9] Cobalt- versus Ruthenium-Catalyzed Alder-Ene Reaction for the Synthesis of Credneramide A and B [J].

Erver, Florian ;

Hilt, Gerhard .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) :5215-5219

[10] A formal synthesis of (-)-cephalotaxine [J].

Esmieu, William R. ;

Worden, Stephen M. ;

Catterick, David ;

Wilson, Claire ;

Hayes, Christopher J. .

ORGANIC LETTERS, 2008, 10 (14) :3045-3048

← 1 2 3 4 →