Lactol-ene reaction: An efficient access to the synthesis of 22R,25-dihydroxy steroid side chains

Koichi Mikami; Hiroyuki Kishino; Hiroyuki Matsueda; Teck Peng Loh

doi:10.1055/s-1993-22504

Lactol-ene reaction: An efficient access to the synthesis of 22R,25-dihydroxy steroid side chains

Koichi Mikami, Hiroyuki Kishino, Hiroyuki Matsueda, Teck Peng Loh

Institute of Science Tokyo

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

4 Scopus citations

Abstract

Lewis acid-promoted carbonyl-ene reaction of steroidal olefin with a new type of enophile, γ-lactol is shown to exhibit high levels of a-diastereofacial selectivity and 20S, 22R-anti diastereoselectivity to afford 22R, 25-dihydroxy steroid side chains featuring insect moulting steroidal hormones, ecdysones and marine steroid, depresosterol.

Original language	English
Pages (from-to)	497-498
Number of pages	2
Journal	Synlett
Volume	1993
Issue number	7
DOIs	https://doi.org/10.1055/s-1993-22504
State	Published - Jul 1993
Externally published	Yes

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10.1055/s-1993-22504

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title = "Lactol-ene reaction: An efficient access to the synthesis of 22R,25-dihydroxy steroid side chains",

abstract = "Lewis acid-promoted carbonyl-ene reaction of steroidal olefin with a new type of enophile, γ-lactol is shown to exhibit high levels of a-diastereofacial selectivity and 20S, 22R-anti diastereoselectivity to afford 22R, 25-dihydroxy steroid side chains featuring insect moulting steroidal hormones, ecdysones and marine steroid, depresosterol.",

author = "Koichi Mikami and Hiroyuki Kishino and Hiroyuki Matsueda and Loh, {Teck Peng}",

year = "1993",

month = jul,

doi = "10.1055/s-1993-22504",

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T2 - An efficient access to the synthesis of 22R,25-dihydroxy steroid side chains

AU - Mikami, Koichi

AU - Kishino, Hiroyuki

AU - Matsueda, Hiroyuki

AU - Loh, Teck Peng

PY - 1993/7

Y1 - 1993/7

N2 - Lewis acid-promoted carbonyl-ene reaction of steroidal olefin with a new type of enophile, γ-lactol is shown to exhibit high levels of a-diastereofacial selectivity and 20S, 22R-anti diastereoselectivity to afford 22R, 25-dihydroxy steroid side chains featuring insect moulting steroidal hormones, ecdysones and marine steroid, depresosterol.

AB - Lewis acid-promoted carbonyl-ene reaction of steroidal olefin with a new type of enophile, γ-lactol is shown to exhibit high levels of a-diastereofacial selectivity and 20S, 22R-anti diastereoselectivity to afford 22R, 25-dihydroxy steroid side chains featuring insect moulting steroidal hormones, ecdysones and marine steroid, depresosterol.

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DO - 10.1055/s-1993-22504

M3 - 文章

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SN - 0936-5214

VL - 1993

SP - 497

EP - 498

JO - Synlett

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ER -

Lactol-ene reaction: An efficient access to the synthesis of 22R,25-dihydroxy steroid side chains

Abstract

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