Synthesis of Enantiomerically Pure 24-Alkylsterol Side Chains, in Both Enantiomeric Forms, Starting from (R)-( + )-Limonene

Francesco Nicotra; Luigi Panza; Fiamma Ronchetti; Giovanni Russo; Lucio Toma

doi:10.1021/jo00358a020

Synthesis of Enantiomerically Pure 24-Alkylsterol Side Chains, in Both Enantiomeric Forms, Starting from (R)-( + )-Limonene

Francesco Nicotra
, Luigi Panza
, Fiamma Ronchetti
, Giovanni Russo
, Lucio Toma

Research output: Contribution to journal › Article › peer-review

Abstract

Three couples of enantiomeric synthons corresponding to six 24-alkylsterol side chains, (R)- and (S)-1-bromo-3,4-dimethylpentane, (R)- and (S)-1-bromo-3-ethyl-4-methylpentane, and (R)- and (S)-5-(acetyloxy)-1-bromo-3-(1-methylethyl)pentane, were synthesized from the same chiral intermediate, (R)-5-(acyloxy)-3-(1-methylethyl)pentan-1-ol, readily obtainable from (R)-(+)-limonene.

Original language	English
Pages (from-to)	1272-1276
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	51
Issue number	8
DOIs	https://doi.org/10.1021/jo00358a020
Publication status	Published - 1986
Externally published	Yes

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title = "Synthesis of Enantiomerically Pure 24-Alkylsterol Side Chains, in Both Enantiomeric Forms, Starting from (R)-( + )-Limonene",

abstract = "Three couples of enantiomeric synthons corresponding to six 24-alkylsterol side chains, (R)- and (S)-1-bromo-3,4-dimethylpentane, (R)- and (S)-1-bromo-3-ethyl-4-methylpentane, and (R)- and (S)-5-(acetyloxy)-1-bromo-3-(1-methylethyl)pentane, were synthesized from the same chiral intermediate, (R)-5-(acyloxy)-3-(1-methylethyl)pentan-1-ol, readily obtainable from (R)-(+)-limonene.",

author = "Francesco Nicotra and Luigi Panza and Fiamma Ronchetti and Giovanni Russo and Lucio Toma",

year = "1986",

doi = "10.1021/jo00358a020",

language = "English",

volume = "51",

pages = "1272--1276",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Synthesis of Enantiomerically Pure 24-Alkylsterol Side Chains, in Both Enantiomeric Forms, Starting from (R)-( + )-Limonene

AU - Nicotra, Francesco

AU - Panza, Luigi

AU - Ronchetti, Fiamma

AU - Russo, Giovanni

AU - Toma, Lucio

PY - 1986

Y1 - 1986

N2 - Three couples of enantiomeric synthons corresponding to six 24-alkylsterol side chains, (R)- and (S)-1-bromo-3,4-dimethylpentane, (R)- and (S)-1-bromo-3-ethyl-4-methylpentane, and (R)- and (S)-5-(acetyloxy)-1-bromo-3-(1-methylethyl)pentane, were synthesized from the same chiral intermediate, (R)-5-(acyloxy)-3-(1-methylethyl)pentan-1-ol, readily obtainable from (R)-(+)-limonene.

AB - Three couples of enantiomeric synthons corresponding to six 24-alkylsterol side chains, (R)- and (S)-1-bromo-3,4-dimethylpentane, (R)- and (S)-1-bromo-3-ethyl-4-methylpentane, and (R)- and (S)-5-(acetyloxy)-1-bromo-3-(1-methylethyl)pentane, were synthesized from the same chiral intermediate, (R)-5-(acyloxy)-3-(1-methylethyl)pentan-1-ol, readily obtainable from (R)-(+)-limonene.

UR - https://www.scopus.com/pages/publications/9244220563

U2 - 10.1021/jo00358a020

DO - 10.1021/jo00358a020

M3 - Article

SN - 0022-3263

VL - 51

SP - 1272

EP - 1276

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Synthesis of Enantiomerically Pure 24-Alkylsterol Side Chains, in Both Enantiomeric Forms, Starting from (R)-( + )-Limonene

Abstract

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