α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes

Köhler, Thomas; Huhn, Thomas; Groth, Ulrich

doi:10.17721/fujcV3I1P29-45

α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes

Тип публікації :

Стаття

Дата випуску :

2015

Автор(и) :

Köhler, Thomas

Huhn, Thomas

Groth, Ulrich

Мова основного тексту :

Англійська

eKNUTSHIR URL :

https://ir.library.knu.ua/handle/15071834/25580

DOI :

10.17721/fujcV3I1P29-45

Журнал :

French-Ukrainian Journal of Chemistry

Том :

3

Випуск :

1

ISSN :

2312-3222

Початкова сторінка :

29

Кінцева сторінка :

45

Цитування :

[APA 7] Köhler, T., Huhn, T., & Groth, U. (2015). α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes. French-Ukrainian Journal of Chemistry, 3(1), 29–45. https://doi.org/10.17721/fujcV3I1P29-45

[ДСТУ] Köhler T., Huhn T., Groth U. α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes. French-Ukrainian Journal of Chemistry. 2015. Vol. 3, no. 1. P. 29—45. DOI: 10.17721/fujcV3I1P29-45 (date of access: 18.07.2026).

Hexahydroindenes 10 are readily available in 3 steps with an overall yield of 41 – 45 % starting from the Hajos Wiechert ketone 1. Alkylation of the α,β-unsaturated ketone 1 at C-4 has been achieved by thioalkylation of the corresponding zinc dienolate 2 with α-chlorosulfides of type 3. Subsequent in situ reduction and desulfurization of the β-(phenylthio) ketones 4 leads directly to the 4-substituted hexahydroindene-5-ols 6 which can be deoxygenated via their mesylates to the hexahydroindenes 10.

Ключові слова :

Zinc dienolates Thioalkylation of Indene derivatives Steroids

Файл(и) :

Формат :

Adobe PDF

Розмір :

668.96 KB

Контрольна сума :

(MD5):eff7b86451ddff6ac027d097eb658732

Якщо не вказано інше, ця робота розповсюджується на умовах ліцензії Creative Commons Attribution 4.0 International