Synthesis and structure elucidation of a novel ecdysteroid, gerardiasterone

Honda, Toshio; Takada, Hironao; Miki, Shigehiro; Tsubuki, Masayoshi

doi:10.1016/s0040-4039(00)61409-0

Cited by 24 publications

(8 citation statements)

References 17 publications

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“…cause allergic reactions, the symptoms of which are headaches, nose itching, and rashes).291 A sesquiterpene hydrocarbon(403) and a diterpene hydrocarbon(404) were both obtained from a Western Australian Higginsia species 292. The isonitrile(405) from Halichondria sp.293 has been synthesized using an ally1 cyanate-to-isocyanate rearrangement.2g4 Two new linear diterpene diols, (406) and (407), were isolated from the Caribbean sponge Myrmekioderma styx and were shown to be toxic to brine shrimp 295.…”

mentioning

confidence: 99%

Marine natural products

Faulkner¹

1995

Nat. Prod. Rep.

316

264

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mentioning

confidence: 99%

Marine natural products

Faulkner¹

1995

Nat. Prod. Rep.

316

264

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“…Osmium-mediated dihydroxylation was only productive with stoichiometric amounts of osmium tetroxide in a pyridine/water mixture at 65°C. [27] In this way a single diol 29 was obtained. From 1 H NMR NOE measurements it was clear that the dihydroxylation had taken place from the more open endo face of the alkene.…”

Section: Second Approach: [2+2] Photocycloaddition Of Allene Butenolidesmentioning

confidence: 99%

Synthesis of the Tricyclic Core of Solanoeclepin A through Intramolecular [2+2] Photocycloaddition of an Allene Butenolide

et al. 2005

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Studies are reported towards the synthesis of solanoeclepin A (1), the hatching agent of potato cyst nematodes. Two approaches are investigated to access the tricyclic core including the intricate bicyclo[2.1.1]hexanone moiety. The first approach is based on the intramolecular [2+2] photocycloaddition of dioxenone butenolide 10 and is shown to be less practical due to the limited synthetic utility of the photoproduct 11. The second approach uses as the key step the intramolecular [2+2] photocycloaddition reaction of allene butenolide 39. This latter photosubstrate is prepared through silver-mediated coupling of silyloxyfuran 9 and allenic bromide

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“…16 In this way a single diol 16 was obtained. Osmium-mediated dihydroxylation was only productive with stoichiometric amounts of osmium tetroxide in a pyridine/ water mixture at 65 ЊC.…”

Section: Scheme 1 Retrosynthesis Of Solanoeclepin a (Arbitrary Protecmentioning

confidence: 99%

“…Osmium-mediated dihydroxylation was only productive with stoichiometric amounts of osmium tetroxide in a pyridine/ water mixture at 65 ЊC. 16 In this way a single diol 16 was obtained. From 1 H NMR NOE measurements it was clear that the dihydroxylation had taken place from the more open endo face of the alkene.…”

Section: Doi: 101039/ B311415ementioning

confidence: 99%