ChemInform Abstract: Studies for a Diastereoselective Synthesis of the Tetracyclic Diterpenic Diol Stemarin. An Improved Procedure for the Synthesis of 8( 9)‐Podocarpen‐14‐ones: The Total Synthesis of 18‐Benzyloxy‐8(9)‐ podocarpen‐14‐one and Related Studies.

Antonaroli, Simonetta; Berettoni, Marco; Cifarelli, G.; Lupi, Alessandro; Bettolo, Rinaldo Marini; Romeo, Sergio

doi:10.1002/chin.199236242

Cited by 4 publications

(21 citation statements)

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“…Comparison of the NMR data recorded by us for (+)-1 and those reported in the literature for 1 2,30,31 showed differences (Table 1) particularly in the 13 C NMR regarding C(5), C(7), C(8), C (11), C (12), C (15), and C( 16).…”

Section: ■ Results and Discussionmentioning

confidence: 61%

“…Compound (+)-1 was fully characterized by means of 1 H NMR, 13 C NMR, COSY, HSQC, HMBC, DEPT 135, and NOESY experiments (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Thus, in the frame of our efforts in the synthesis of bicyclo[3.2.1]octane diterpene alkaloids − and diterpenoids, − having now in hand a simple approach for the construction of the C/D ring system of the stemarane diterpenes, we decided to clarify this stereochemical aspect of Chilean stemarane diterpenes by synthesizing (+)-2-deoxyoryzalexin S ( 1 ) from the preformed system of (+)-podocarpic acid. The original isolated material is, in fact, no longer available for direct comparison ( vide infra ).…”

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confidence: 99%

“…I n 1990 Garbarino and co-workers in Chile isolated a diterpenoid from some Calceolaria species 1−3 to which, on the basis of the 1 H and 13 C spectra, the structure of 1 (2deoxyoryzalexin S) was attributed. To this compound, as well as to its congeners, the absolute ent-stemarane configuration was assigned on biogenetic grounds.…”

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confidence: 99%

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Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer

et al. 2012

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(+)-2-Deoxyoryzalexin S (1), the nominal enantiomer of a diterpenoid isolated in Chile from Calceolaria species, was regio- and diastereoselectively synthesized from (+)-podocarpic acid. (+)-2-Deoxyoryzalexin S (1) was characterized also as its acetyl derivative, (+)-2, whose structure was confirmed by X-ray crystallographic analysis. Surprisingly, comparison of the data recorded for (+)-1 and (+)-2 and those reported in the literature for the Calceolaria isolated diterpenoid 1 and its derivative (-)-2 showed some differences, suggesting that the latter do not possess the proposed structures.

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Section: ■ Results and Discussionmentioning

confidence: 61%

“…Compound (+)-1 was fully characterized by means of 1 H NMR, 13 C NMR, COSY, HSQC, HMBC, DEPT 135, and NOESY experiments (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer

et al. 2012

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“…Surprisingly, after a successful preparation of the 8(9)podocarpen-14-one intermediate 46 [80] and a model work [81], the allene photoaddition to 8(9)-podocarpen-14-one 55 , obtained from known 52 [82,83], gave, along the expected cyclo-photoadduct 57 , compound 59 [84]. Compound 59 is the result of the H-C(5) abstraction by the initially side chain radical 56 , to give the Cope rearrangement like intermediate 58 , followed by homolytic cleavage of the C(9)-C(10) bond (Scheme 9).…”

Section: Synthesismentioning

confidence: 99%

Stemarane Diterpenes and Diterpenoids

Leonelli

Valletta

Migneco

et al. 2019

IJMS

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In this article the scientific activity carried out on stemarane diterpenes and diterpenoids, isolated over the world from various natural sources, was reviewed. The structure elucidation of stemarane diterpenes and diterpenoids was reported, in addition to their biogenesis and biosynthesis. Stemarane diterpenes and diterpenoids biotransformations and biological activity was also taken into account. Finally the work leading to the synthesis and enantiosynthesis of stemarane diterpenes and diterpenoids was described.

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Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin

et al. 2011

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The problem of constructing diastereoselectively the C/D ring system of stemarane diterpenes from a bicyclo[2.2.2]octane intermediate was solved resulting in very simple synthesis of (+)-13-stemarene 1. The obtaining of the latter represents also a formal synthesis of (+)-18-deoxystemarin 2. In the key step, the epimeric mixture 10, dissolved in toluene, was converted by the action of TsOH into (+)-stemar-13-en-15-one 28.

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ChemInform Abstract: Studies for a Diastereoselective Synthesis of the Tetracyclic Diterpenic Diol Stemarin. An Improved Procedure for the Synthesis of 8( 9)‐Podocarpen‐14‐ones: The Total Synthesis of 18‐Benzyloxy‐8(9)‐ podocarpen‐14‐one and Related Studies.

Cited by 4 publications

References 0 publications

Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer

Regio- and Diastereoselective Synthesis and X-ray Structure Determination of (+)-2-Deoxyoryzalexin S from (+)-Podocarpic Acid. Structural Nonidentity with Its Nominal Natural Isolated Enantiomer

Stemarane Diterpenes and Diterpenoids

Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin

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