The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol

The synthetic challenges associated with the selective synthesis of ?-Santalene (1), (Z)-?-Santalol (2), ?-Santalene (3), and most importantly (Z)-?-Santalol (4) have interested the world's synthetic chemists for decades. These molecules, lovely examples of nature's exquisite cre...

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Main Author: Anthony A. Birkbeck
Format: Article
Language:deu
Published: Swiss Chemical Society 2017-12-01
Series:CHIMIA
Subjects:
Online Access:https://www.chimia.ch/chimia/article/view/1690
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author Anthony A. Birkbeck
author_facet Anthony A. Birkbeck
author_sort Anthony A. Birkbeck
collection DOAJ
description The synthetic challenges associated with the selective synthesis of ?-Santalene (1), (Z)-?-Santalol (2), ?-Santalene (3), and most importantly (Z)-?-Santalol (4) have interested the world's synthetic chemists for decades. These molecules, lovely examples of nature's exquisite creations, have been isolated from East Indian Sandalwood Oil (Santalum album L.) and have stimulated chemists to develop new and efficient methodologies to synthesize them. The synthesis and evolution of various approaches to the [2.2.1]bicycloheptane ring system present in ?-Santalene (3) and the even more challenging selective synthesis of the (Z)-allylic alcohol sidechain present in both (Z)-?-Santalol (2) and ((Z)-?-Santalol (4) will be covered in this review.
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spelling doaj.art-3a82253a58e14a358e072d6cf261b7e52022-12-22T00:00:26ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242017-12-01711210.2533/chimia.2017.823The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-SantalolAnthony A. Birkbeck0Firmenich SA, Corporate R&D Division, P.O. Box 239, CH-1211 Geneva 8, Switzerland. alec.birkbeck@firmenich.com The synthetic challenges associated with the selective synthesis of ?-Santalene (1), (Z)-?-Santalol (2), ?-Santalene (3), and most importantly (Z)-?-Santalol (4) have interested the world's synthetic chemists for decades. These molecules, lovely examples of nature's exquisite creations, have been isolated from East Indian Sandalwood Oil (Santalum album L.) and have stimulated chemists to develop new and efficient methodologies to synthesize them. The synthesis and evolution of various approaches to the [2.2.1]bicycloheptane ring system present in ?-Santalene (3) and the even more challenging selective synthesis of the (Z)-allylic alcohol sidechain present in both (Z)-?-Santalol (2) and ((Z)-?-Santalol (4) will be covered in this review. https://www.chimia.ch/chimia/article/view/1690(z)-allylic alcoholSandalwood oilα-santalolβ-santalolSantalum album
spellingShingle Anthony A. Birkbeck
The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
CHIMIA
(z)-allylic alcohol
Sandalwood oil
α-santalol
β-santalol
Santalum album
title The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
title_full The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
title_fullStr The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
title_full_unstemmed The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
title_short The Synthesis of Fragrant Natural Products from Santalum album L.: (+)-(Z)-?-Santalol and (–)-(Z)-?-Santalol
title_sort synthesis of fragrant natural products from santalum album l z santalol and z santalol
topic (z)-allylic alcohol
Sandalwood oil
α-santalol
β-santalol
Santalum album
url https://www.chimia.ch/chimia/article/view/1690
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