Synthesis of (+)-boronolide and (+)-deacetylboronolide using Pd-catalyzed carbonylation and lactonization

被引：6

作者：

Kurogome, Yuji ^{[1
]}

Hattori, Yasunao ^{[2
]}

Makabe, Hidefumi ^{[1
]}

机构：

[1] Shinshu Univ, Grad Sch Agr, Nagano 3994598, Japan

[2] Kyoto Pharmaceut Univ, Dept Med Chem, Yamashina Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 17期

关键词：

Natural products; Lactones; Asymmetric synthesis; Total synthesis; Carbonylation; STEREOSELECTIVE TOTAL-SYNTHESIS; ALPHA-PYRONE; EFFICIENT SYNTHESIS; IBOZA-RIPARIA; BORONOLIDE;

D O I：

10.1016/j.tetlet.2014.03.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Boronolide and (+)-deacetylboronolide were synthesized using Pd-catalyzed CO insertion and lactonization as the key step. As to the C-13 NMR data of (+)-deacetylboronolide, the assignment at C-6 position should be revised. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2822 / 2824

页数：3

共 26 条

[1] Total Synthesis of (-)-Histrionicotoxin
Adachi, Yohei
Kamei, Noriyuki
Yokoshima, Satoshi
Fukuyama, Tohru
[J]. ORGANIC LETTERS, 2011, 13 (16) : 4446 - 4449
[2] Stereoselective total synthesis of (+)-boronolide
Boruwa, J
Barua, NC
[J]. TETRAHEDRON, 2006, 62 (06) : 1193 - 1198
[3] Stereoselective synthesis of (+)-boronolide
Carda, M
Rodríguez, S
Segovia, B
Marco, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) : 6560 - 6563
[4] Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide
Chandrasekhar, M
Chandra, KL
Singh, VK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) : 4039 - 4045
[5] SYNTHESIS OF LACTONES BY THE PALLADIUM-CATALYZED CARBONYLATION OF HALO ALCOHOLS
COWELL, A
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (12) : 4193 - 4198
[6] COWELL A, 1979, TETRAHEDRON LETT, P133
[7] STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE
DAVIESCOLEMAN, MT
RIVETT, DEA
[J]. PHYTOCHEMISTRY, 1987, 26 (11) : 3047 - 3050
[8] Farina V., 2002, HDB ORGANOPALLADIUM, V2, P2351
[9] FRANCA NC, 1971, CR ACAD SCI C CHIM, V273, P439
[10] A stereoselective synthesis of (+)-boronolide
Ghosh, AK
Bilcer, G
[J]. TETRAHEDRON LETTERS, 2000, 41 (07) : 1003 - 1006

← 1 2 3 →