Synthetic photochemistry. LXVII. A total synthesis of (±)-hinesol and (±)-agarospirol via retro-benzilic acid rearrangement

DOI: 10.1246/bcsj.68.2393

Source and publish data:

Bulletin of the Chemical Society of Japan p. 2393 - 2399 (1995)

Update date:2022-08-04

Topics:

Authors:

Hatsui Hatsui

Wang Wang

Takeshita

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1246/bcsj.68.2393

A mild base-catalyzed retro-benzilic acid rearrangement of a proto-photocycloadduct, formed in highly stereoselective photoaddition of methyl 2,4-dioxopentanoate to 1,5-dimethyl-6-methylene-1-cyclohexene, afforded a spiro[4.5]decenedione derivative. Reductive elimination of the α-dicarbonyl function and C₁-homologation furnished (±)-hinesol and (±)-agarospirol.

Full text of DOI:10.1246/bcsj.68.2393

Products guided by the article

Product name:Cyclohexene, 1,5-dimethyl-6-methylene-

Cas No:169898-78-6

R&D Labs maybe for 169898-78-6

QINGDAO NEW FLOURISH INTERNATIOANAL TRADE CO., LTD.

Contact:+86 532 80861829

Address:No. 1, Yinchuan East Road, 266061, Qingdao, China
JiangXi Hong Run Chemical Co., Ltd

Contact:+86-0791-88521351

Address:XingHuo industrial zone in YongXiu county
QINGDAO HONG JIN CHEMICAL CO.,LTD.

website:http://www.hongjinchem.com

Contact:+86-532-83657313

Address:2ND Building, 8 Shangqing Road, Qingdao, Shandong Province, China.
Kraeber & Co GmbH

Contact:+49-4101-3053-0

Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
SuZhou Hua-Emy Chemical Import and Export Co., LTD.

Contact:+86-512-88804994; +86-512-88804550;

Address:710, Building B, International Trade Center, 12 Huanghelu, Changshu, Jiangsu,China

Relevant to this article

Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones

Doi:10.1016/0223-5234(96)88258-4
(1995)
Titanocene(II)-promoted olefination of ω,ω-bis(phenylthio)alkyl alkanoates. A new method for the preparation of ω-hydroxy ketones

Doi:10.1016/S0040-4020(99)01091-1
(2000)
Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol¹)

Doi:10.1248/cpb.49.1581
(2001)
Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: An easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

Doi:10.1039/c4ob00922c
(2014)
H₂O₂-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400

Doi:10.1039/c8gc00381e
(2018)
Atom-efficient synthesis of 2,4,6-trisubstituted 1,3,5-triazinesviaFe-catalyzed cyclization of aldehydes with NH4I as the sole nitrogen source

Doi:10.1039/d0ra03323e
(2020)

Article Doi