Total Synthesis of Acortatarin A Using a Pd(II)-Catalyzed Spiroketalization Strategy

被引：36

作者：

Borrero, Nicholas V. ^{[1
]}

Aponick, Aaron ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 19期

关键词：

AU-CATALYZED CYCLIZATION; DERIVATIVES; ALCOHOLS; DIOLS;

D O I：

10.1021/jo301835e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of acortatarin A relying on a Pd(II)-catalyzed spiroketalization is reported. This strategy allows a single stereocenter in the spiroketalization substrate to produce the target efficiently under mild conditions, installing the necessary oxygenation in the backbone through an allylic transposition. The synthesis also verifies that pollenopyrroside B and acortatarin A are the same compound, and electrochemical studies suggest that the reported bioactivity is not due to simple antioxidant properties.

引用

页码：8410 / 8416

页数：7

共 50 条

[31] Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation
Miyazawa, Yuki
Sugimoto, Makoto
Tanaka-Oda, Ayumi
Makabe, Hidefumi
TETRAHEDRON LETTERS, 2019, 60 (36)
[32] Synthesis of resveratrol using Pd-catalyzed bond formation
Panigot, Michael J.
Zhu, Xijing
Hancock, Catherine
Ward, Amy
McGuire, Holly
Strain, Britton
Anderson, Sierra
Green, Joshua D.
Hargrave, Sarah
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[33] Development of Ferrier(II) carbocyclization catalyzed by Pd(II) and its application to the synthesis of bioactive substances
Takahashi, H
Kittaka, H
Ikegami, S
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2000, 58 (02) : 120 - 128
[34] Synthesis of azanovobiocin derivatives using Cu(I)/Pd(II)-catalyzed C-N bond formation
Moss, Steven M.
Nealmongkol, Prattya
Thasana, Nopporn
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[35] The novel approach to indole alkaloids by using Pd(II)-catalyzed cyclization
Yokoyama, Hajime
Kubo, Takayoshi
Matsumura, Yosuke
Hosokawa, Junichi
Miyazawa, Masahiro
Hirai, Yoshiro
TETRAHEDRON, 2014, 70 (50) : 9530 - 9535
[36] Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates
Karmakar, Ujjwal
Samanta, Rajarshi
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2850 - 2861
[37] Total synthesis of (+)-camptothecin via an intramolecular palladium-catalyzed cyclization strategy
Chavan, Subhash P.
Pathak, Ashok B.
Kalkote, Uttam R.
SYNLETT, 2007, (17) : 2635 - 2638
[38] Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction
Borthakur, Somadrita
Baruah, Swagata
Sarma, Bipul
Gogoi, Sanjib
ORGANIC LETTERS, 2019, 21 (08) : 2768 - 2771
[39] Synthesis of 2,5-Substituted Tetrahydrofurans by Pd(II)-Catalyzed Cyclization
Olszewska, Beata
Kryczka, Boguslaw
Zawisza, Anna
LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (08) : 563 - 567
[40] Synthesis of ε-caprolactone by the Pd(II)-catalyzed carbonylation of penten-1-OL.
Funk, JK
Goldstein, D
Newsham, D
Liu, SS
Sen, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U902 - U902

← 1 2 3 4 5 →