Diterpenoids

Tsutsui, Minoru; Tsutsui, Ethel A.

doi:10.1021/cr50030a003

Cited by 9 publications

(1 citation statement)

References 74 publications

(94 reference statements)

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“…A tabular form of presentation seems to be the most convenient. Good reviews of individual topics are afforded by the following authors: Aneja and coworkers (6), hemiterpenes; Haagen-Smit (7,8), lower terpenes, sesquiterpenes, and diterpenes; Jeger (9), triterpenes; Jones and Halsall (10), tetracyclic triterpenes; Steiner and Holtzem (11), triterpenes; and Tsutsui and Tsutsui (12), diterpenes. For this reason, reference has been made in the table to standard works, such as those of Simonsen (1), Guenther (2), Gildemeister (3), de Mayo (4), and Karrer (5).…”

Section: Structure and Distribution Of Terpenoidsmentioning

confidence: 99%

Terpenoids: Structure and Distribution

Sandermann¹

1962

Comparative Biochemistry

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Section: Structure and Distribution Of Terpenoidsmentioning

confidence: 99%

Terpenoids: Structure and Distribution

Sandermann¹

1962

Comparative Biochemistry

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Ein neues Diterpen aus Salvia officinalis L. und eine Notiz zur Konstitution von Pikrosalvin

Linde

1964

Helvetica Chimica Acta

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Aus den Blättern von Salvia officinalis L. konnte eine neue Diterpen‐diphenol‐carbonsäure (äls Diacetylverbindung) isoliert und in ihrer Konstitution aufgeklärt werden. Durch eine relativ einfache und übersichtlich verlaufende Reaktionsfolge liess sich eine Verknüpfung rnit dem in derselben Pflanzenart von BRIESKORN et al. aufgefundenen Pikrosalvin erzielen, womit die von diesen Autoren postulierte Konstitution XIII (vgl. [6]) für Pikrosalvin im Sinne der Formel XIV modifiziert werden sollte. Pikrosalvin selbst liess sich in dem untersuchten Drogenmuster nicht auffinden.

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Chemical Transformations of Phyllocladane (=13β‐Kaurane) Diterpenoids

Liu

Müller

Rüedi

2003

Helvetica Chimica Acta

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Earlier phytochemical work on Plectranthus ambiguus (Lamiaceae) afforded a series of tetracyclic phyllocladane-type ( 13b-kaurane) diterpenoids (see 1a ± f). In the course of investigations concerning the reaction behavior of this rare natural-products, a new constituent of P. ambiguus was isolated, (2S,3R,16R)-phyllocladane-2,3,16,17-tetrol 2,3-diacetate (1g), and another eighteen new phyllocladanes were prepared by chemical transformations and characterized. The main constituent 1b of P. ambiguus was chemically transformed to the known natural diterpenoid calliterpenone ( (16R)-16,17-dihydroxyphyllocladan-3-one; 2) thus unambiguously establishing its structure (Scheme 1). Epimerization at C(16) via the epoxy derivative 20 yielded 16-epicalliterpenone (21), 17-hydroxyphylloclad-15-ene-3-one (22), and (16R)-3-oxophyllocladan-17-al (23) (Scheme 6). Comparing this reaction sequence with the corresponding one starting from diastereoisomeric (16R)-16,17-dihydroxy-ent-kauran-3-one ( abbeokutone; 27) showed basically the same outcome (Scheme 7). Furthermore, three new C(16)-substituted ent-kauran-3-ones were characterized.Reliable spectroscopic arguments for the determination of the configuration at C(16) in phyllocladanes and kauranes as well as for the differentiation of the diastereoisomeric skeletons are presented.

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Diterpenoids

Cited by 9 publications

References 74 publications

Terpenoids: Structure and Distribution

Terpenoids: Structure and Distribution

Ein neues Diterpen aus Salvia officinalis L. und eine Notiz zur Konstitution von Pikrosalvin

Chemical Transformations of Phyllocladane (=13β‐Kaurane) Diterpenoids

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