Total Synthesis of Naphterpin and Marinone Natural Products

被引：20

作者：

Murray, Lauren A. M. ^{[1
]}

Fallon, Thomas ^{[1
]}

Sumby, Christopher J. ^{[1
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 20期

基金：

澳大利亚研究理事会;

关键词：

STRUCTURAL ELUCIDATION; BIOMIMETIC SYNTHESIS; NAPHTHOQUINONES; MEROCHLORINS; BIOSYNTHESIS; ANTIBIOTICS;

D O I：

10.1021/acs.orglett.9b03095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6 pi-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

引用

页码：8312 / 8315

页数：4

共 47 条

[31]

SAVARD J, 1979, TETRAHEDRON LETT, P4911

[32] Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone [J].

Schnell, Simon D. ;

Linden, Anthony ;

Gademann, Karl .

ORGANIC LETTERS, 2019, 21 (04) :1144-1147

[33]

SHIN-YA K, 1990, Tetrahedron Letters, V31, P6025, DOI 10.1016/S0040-4039(00)98019-5

[34] 7-DEMETHYLNAPHTERPIN, A NEW FREE-RADICAL SCAVENGER FROM STREPTOMYCES-PRUNICOLOR [J].

SHINYA, K ;

SHIMAZU, A ;

HAYAKAWA, Y ;

SETO, H .

JOURNAL OF ANTIBIOTICS, 1992, 45 (01) :124-125

[35] ISOLATION AND STRUCTURAL ELUCIDATION OF AN ANTIOXIDATIVE AGENT, NAPHTERPIN [J].

SHINYA, K ;

IMAI, S ;

FURIHATA, K ;

HAYAKAWA, Y ;

KATO, Y ;

VANDUYNE, GD ;

CLARDY, J ;

SETO, H .

JOURNAL OF ANTIBIOTICS, 1990, 43 (04) :444-447

[36] Enantioselective Total Synthesis of (-)-Napyradiomycin A1 via Asymmetric Chlorination of an Isolated Olefin [J].

Snyder, Scott A. ;

Tang, Zhen-Yu ;

Gupta, Ritu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (16) :5744-+

[37] Studies on terpenoids produced by actinomycetes - Isolation and structural elucidation of antioxidative agents, naphterpins B and C [J].

Takagi, H ;

Motohashi, K ;

Miyamoto, T ;

Shin-Ya, K ;

Furihata, K ;

Seto, H .

JOURNAL OF ANTIBIOTICS, 2005, 58 (04) :275-278

[38] A concise total synthesis of (±)-A80915G, a member of the napyradiomycin family of antibiotics [J].

Takemura, S ;

Hirayama, A ;

Tokunaga, J ;

Kawamura, F ;

Inagaki, K ;

Hashimoto, K ;

Nakata, M .

TETRAHEDRON LETTERS, 1999, 40 (42) :7501-7505

[39] A Diels-Alder strategy towards a benzonaphthopyranoquinone [J].

Tapia, RA ;

Alegría, L ;

Valderrama, JA ;

Cortés, M ;

Pautet, F ;

Fillion, H .

TETRAHEDRON LETTERS, 2001, 42 (05) :887-889

[40] The first total synthesis of (±)-napyradiomycin A1 [J].

Tatsuta, K ;

Tanaka, Y ;

Kojima, M ;

Ikegami, H .

CHEMISTRY LETTERS, 2002, (01) :14-15

← 1 2 3 4 5 →