Icetexane Diterpenoids Research Articles

Ga(III)-Catalyzed Cycloisomerization Approach to (±)-Icetexone and (±)-epi-Icetexone

A Ga(III)-catalyzed cycloisomerization reaction provides expedient access to a benzannulated cycloheptadiene bearing a cyano group, which has been applied to the syntheses of several icetexane diterpenoids including icetexone and epi-icetexone. Key to the synthesis is a novel in situ generated diazene rearrangement.

An epoxide ring-opening approach for a short and stereoselective synthesis of icetexane diterpenoids

A new approach for the synthesis of the core skeleton of icetexane diterpenoids is presented and deals with an epoxide ring-opening reaction by metallated aromatic compounds. Employing this strategy, a short synthesis of an icetexane analogue of brussonol was achieved in just four steps from 2-allyl-cyclohexanone.

Three New Diterpenoids from Salvia przewalskiiMaxim

Abstractmagnified imageThree new compounds including one ortho‐quinone‐type icetexane diterpenoid, i.e., przewalskin E (1), one abietane dinorditerpenoid, i.e., przewalskin F (2), and one 7,20‐epoxyabietane diterpenoid, i.e., przewalskin G (3), were isolated from Salvia przewalskii Maxim. The identification and structure elucidation of these compounds were based on 1D‐ and 2D‐NMR spectral‐data analysis. It is noteworthy that przewalskin E (1), featured with an 11,12‐dioxoicetexane skeleton, represents the second example of a naturally occurring ortho‐quinone‐type icetexane diterpenoid from Salvia plants.

Structure, biosynthetic relationships and chemical synthesis of the icetexane diterpenoids

Covering: up to 2009A detailed overview of the icetexane diterpenoid natural product family is presented. The structure, isolation and biological activity of these natural products is followed by an examination of their biosynthetic relationships and a comprehensive summary of the synthetic approaches to the icetexane family; 92 references are cited.

Reconciling Icetexane Biosynthetic Connections with Their Chemical Synthesis: Total Synthesis of (±)-5,6-Dihydro-6α-hydroxysalviasperanol, (±)-Brussonol, and (±)-Abrotanone

A unified strategy for the chemical synthesis of the icetexane diterpenoids brussonol and 5,6-dihydro-6alpha-hydroxysalviasperanol has led to a structural revision of the recently isolated natural products abrotandiol and abrotanone.

Ga(III)-Catalyzed Cycloisomerization Strategy for the Synthesis of Icetexane Diterpenoids: Total Synthesis of (±)-Salviasperanol

[reaction: see text] A general approach to the tricyclic core of the icetexane natural products via the cycloisomerization of alkynyl indenes using GaCl(3) is presented. This strategy provides an efficient synthesis of the natural product salviasperanol and sets the stage for access to other members of this family of diterpenoids.

Two New Icetexane Diterpenoids from Salvia przewalskii.

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Rearranged icetexane diterpenoids from the roots of Salvia thymoides (Labiatae)

From the roots of Salvia thymoides Benth., three new rearranged icetexane diterpenoids (2–4) were isolated together with the previously described quinone tilifolidione (1). The proposed structures were established by extensive NMR analysis, including HMBC and HMQC pulse sequences.

Two New Icetexane Diterpenoids from Salvia przewalskii

Two new icetexane diterpenoids, przewalskin C, D (1, 2), together with sixteen known diterpenoids, were isolated from Salvia przewalskii. Eight of known ones (compounds 3, 12-18) were reported firstly from this plant. To the best of our knowledge, it's the first report of icetexane diterpenoids from this plant. The identification and structural elucidation of these compounds were based on 1D- and 2D-NMR spectral data analysis.

Abietane and icetexane diterpenoids from Salvia ballotaeflora and Salvia axillaris

From the aereal parts of Salvia ballotaeflora three new icetexane diterpenoids were isolated besides anastomosine and conacytone. The structure of these compounds were established as 19-deoxyicetexone, 19-deoxyisoicetexone and 7,20-dihydroanastomosine by spectroscopic means. Cryptotanshinone was the sole diterpenoid isolated from both aerial parts and roots of S. axillaris.

Abietane and Icetexane Diterpenoids from Salvia Pubescens

The aerial parts of Salvia pubescens afforded, besides icetexone and methylconacytone, a new icetexane diterpenoid named 19(R)-acetoxy-19-deoxoicetexone. Its structure was elucidated by spectroscopic methods and chemical correlation with icetexone.

Abietane and icetexane diterpenoids from the roots of Salvia aspera

From the roots of Salvia aspera, two new icetexane diterpenoids (salviasperanol and 5,6-dihidro-6α-hydroxysalviasperanol) and one new abietane derivative (6-epi-demethylesquirolin D) were isolated in addition to the previously known diterpenoids sugiol, taxodione and demethylsalvicanol. The structures of the new compounds were established by spectroscopic means. An X-ray analysis was performed on salviasperanol.

Abietane and icetexane diterpenoids from Salvia candicans

Seven abietane and icetexane diterpenoids were isolated from the aerial parts of Salvia candicans. Three were identified as conacytone, icetexone and anastomosine. The other four were new diterpenes, whose structures were established by spectroscopic and chemical means. Two of them had an icetexane skeleton.