NDLI: Ent-kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations

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2-halogen-substituted pyridinium-N-phenacylides and their cycloiminium and acyclic analogs: 1. Synthesis of the parent salts, their betaine-ylides, and oxazolium analogs

Review Journal of Chemistry : Volume 1, Issue 1, January 2011

Ent-kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations

Content Provider	Springer Nature Link
Author	Kataev, E. Khaybullin, R. N. Sharipova, R. R. Strobykina, I. Yu.
Copyright Year	2011
Abstract	This review is devoted to ent-kaurane diterpenoids and related glycosides, which represent two naturally occurring groups of compounds with interesting structures and properties. Much useful information about the biogenesis and biological activities of these compounds is presented; however, the greatest part of the review covers various aspects of the chemical transformations of native ent-kaurane diterpenoids, namely, their reactions via COOH, C=O, and OH groups and double bonds. Special attention is given to rearrangements of the carbon skeleton, primarily the Wagner-Meerwein rearrangement of the well-known kaurane diterpenoid steviol into its isomer, the well-known ent-beyerane diterpenoid isosteviol. A separate section is devoted to the chemical transformations of isosteviol, which are used to demonstrate how the well-known reactions of COOH and C=O groups, as well as CH$_{2}$-C(O)R fragments, proceed in unusual ways when these moieties are attached to rigid hydrocarbon skeletons of naturally occurring compounds (or when they are parts of them). The final section considers ent-kaurane glycosides, focusing on those isolated from the plant Stevia rebaudiana, which is well known because they are 300–400 times sweeter than sucrose. The chemical transformations and, in some cases, biotransformations of these compounds (rebaudiosides) are described in detail, including the total synthesis of some rebaudiosides aimed at creating a production technology for low-calorie sweeteners. The review covers data published between 1964 and 2010, including original results obtained by the authors.
Starting Page	93
Ending Page	160
Page Count	68
File Format	PDF
ISSN	20799780
Journal	Review Journal of Chemistry
Volume Number	1
Issue Number	2
e-ISSN	20799799
Language	English
Publisher	SP MAIK Nauka/Interperiodica
Publisher Date	2011-06-03
Publisher Place	Dordrecht
Access Restriction	Subscribed
Subject Keyword	kauranes beyeranes glycosides diterpenoids steviol isosteviol S. rebaudiana steviolbioside Chemistry/Food Science
Content Type	Text
Resource Type	Article

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