Synthesis and Evaluation of Habiterpenol Analogs

Konya, Miyuki; Arima, Shiho; Lee, Daiki; Ohtawa, Masaki; Shimoyama, Kenta; Fukuda, Takashi; Uchida, Ryuji; Tomoda, Hiroshi; Yamaotsu, Noriyuki; Tanaka, Nobutada; Nagamitsu, Tohru

doi:10.1248/cpb.c21-00993

Cited by 3 publications

(1 citation statement)

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“…This enabled the determination of the absolute configuration of 1 and the syntheses of 7-epi-1 and some habiterpenol analogs for a structure-activity relationship (SAR) study. 8 To further improve the synthetic method, we developed a concise route, where the key reactions involved the coupling of the achiral indene 6 (DEring unit), which could be easily derived in a few steps, with aldehyde 7 (AB-ring unit) 9 and the construction of the C ring through radical cyclization initiated by metal hydride hydrogen atom transfer (MHAT) 10 (Scheme 1B). Indene 6, which has a bulky and easily removable TMS group, would undergo the regioselective coupling reaction with aldehyde 7 to construct the C3 quaternary stereocenter.…”

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Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

et al. 2023

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confidence: 99%

Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

et al. 2023

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Ring‐Opening Reactions of Epoxides With Titanium(III) Reagents

RajanBabu¹,

Nugent²,

Halder³

2022

Organic Reactions

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The ring‐opening reactions of epoxides with titanium(III) reagents such as Cp 2 TiCl are critically reviewed, including the scope, limitations, and mechanism of these synthetically useful transformations. The initial reaction proceeds by single‐electron transfer to give a carbon‐centered β‐titanoxy radical. The resulting radical can be terminated by a number of different reaction pathways, including epoxide deoxygenation, reduction to the alcohol, intermolecular addition to activated olefins, and intramolecular addition (cyclization). The literature is surveyed from the first reported examples in 1988 through October, 2021.

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Comprehensive Studies on the Synthetic Organic Chemistry of Unique Bioactive Natural Products; Total Synthesis, Drug Discovery, and Development of New Reactions

Ohtawa

2022

YAKUGAKU ZASSHI

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Research on natural product chemistry via organic chemistry ranges from isolation and structural elucidation to total synthesis, drug discovery, and chemical biology. Discoveries in organic chemistry, such as novel reactions and synthetic strategies, are enabled by the studies of total synthesis. Thus, organic (synthetic) chemistry and natural product chemistry are correlated. We conducted comprehensive studies, including structure-activity relationship, drug discovery, and total synthesis studies, on the synthetic organic chemistry of natural products with unique biological activities and the development of novel reactions discovered through these products. This review describes the total synthesis of simpotentin, a novel potentiator of amphotericin B, and the development of the novel lactonization reactions of homopropargyl alcohols via intramolecular ketene trapping.

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Synthesis and Evaluation of Habiterpenol Analogs

Cited by 3 publications

References 15 publications

Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

Ring‐Opening Reactions of Epoxides With Titanium(III) Reagents

Comprehensive Studies on the Synthetic Organic Chemistry of Unique Bioactive Natural Products; Total Synthesis, Drug Discovery, and Development of New Reactions

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