Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation
Tiziana Benincori
1
,
Silvana Bruno
2
,
Giuseppe Celentano
3
,
Tullio Pilati
4
,
Alessandro Ponti
4
,
Simona Rizzo
4
,
Mara Sada
5
,
Francesco Sannicolò
4
1
Dipartimento di Scienze Chimiche ed Ambientali dell'Università dell'Insubria, via Valleggio, 11, I‐22100 Como
|
3
Istituto di Chimica Organica Alessandro Marchesini dell'Università, via Venezian, 21, I‐20133 Milano
4
Istituto di Scienze e Tecnologie Molecolari, Consiglio Nazionale delle Ricerche, via C. Golgi, 19, I‐20133 Milano
5
Dipartimento di Chimica Organica e Industriale dell'Università, via Venezian, 21, I‐20133 Milano (phone: +39‐0250‐314‐174, fax: +39‐0250‐314‐139
Publication type: Journal Article
Publication date: 2005-07-20
scimago Q2
wos Q3
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A process-scale stereoselective synthesis of nature-identical (−)-(S,S)-7-hydroxycalamenal (=(−)-(5S,8S)-5,6,7,8-tetrahydro-3-hydroxy-5-methyl-8-(1-methylethyl)naphthalene-2-carbaldehyde; (−)-1a) in 96% enantiomeric excess (ee) with the aid of chiral Ru complexes has been developed. The key step was the enantioselective hydrogenation of easily accessible 2-(4-methoxyphenyl)-3-methylbut-2-enoic acid (10) to (+)-11 in a 86% ee (Scheme 5 and Table 1). A substantial increase in optical purity (96% ee) was achieved by induced crystallization of the intermediate (+)-3,4-dihydro-4-(1-methylethyl)-7-methoxy-2H-naphthalen-1-one ((+)-3). Computational conformation analysis carried out on the analog (−)-9 rationalized the high diastereoselectivity achieved in the catalytic hydrogenation of the CC bond.
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Benincori T. et al. Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation // Helvetica Chimica Acta. 2005. Vol. 88. No. 7. pp. 1776-1789.
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Benincori T., Bruno S., Celentano G., Pilati T., Ponti A., Rizzo S., Sada M., Sannicolò F. Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation // Helvetica Chimica Acta. 2005. Vol. 88. No. 7. pp. 1776-1789.
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TY - JOUR
DO - 10.1002/hlca.200590139
UR - https://doi.org/10.1002/hlca.200590139
TI - Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation
T2 - Helvetica Chimica Acta
AU - Benincori, Tiziana
AU - Bruno, Silvana
AU - Celentano, Giuseppe
AU - Pilati, Tullio
AU - Ponti, Alessandro
AU - Rizzo, Simona
AU - Sada, Mara
AU - Sannicolò, Francesco
PY - 2005
DA - 2005/07/20
PB - Wiley
SP - 1776-1789
IS - 7
VL - 88
SN - 0018-019X
SN - 1522-2675
ER -
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@article{2005_Benincori,
author = {Tiziana Benincori and Silvana Bruno and Giuseppe Celentano and Tullio Pilati and Alessandro Ponti and Simona Rizzo and Mara Sada and Francesco Sannicolò},
title = {Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation},
journal = {Helvetica Chimica Acta},
year = {2005},
volume = {88},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/hlca.200590139},
number = {7},
pages = {1776--1789},
doi = {10.1002/hlca.200590139}
}
Cite this
MLA
Copy
Benincori, Tiziana, et al. “Process-Scale Total Synthesis of Nature-Identical (−)-(S,S)-7-Hydroxycalamenal in High Enantiomeric Purity through Catalytic Enantioselective Hydrogenation.” Helvetica Chimica Acta, vol. 88, no. 7, Jul. 2005, pp. 1776-1789. https://doi.org/10.1002/hlca.200590139.