A McMurry Route to the Dienediyne Portion of Models of the Neocarzinostatin Chromophore

Rank, Elisabeth; Brückner, Reinhard

doi:10.1002/(sici)1099-0690(199806)1998:6<1045::aid-ejoc1045>3.0.co;2-o

Cited by 12 publications

(4 citation statements)

References 86 publications

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“…The tetraene 80, which was investigated as a tetradentate ligand for transition metals, accommodates an Ag þ ion within the cavity to give a unique square-planar com- plex [106]. Several polycyclic dienediynes and trienediynes, such as 81 and 82, have been synthesized as models of the antitumor agent neocarzinostatin chromophore [107][108][109][110][111].…”

Section: Intermolecular Cross-coupling Reactionsmentioning

confidence: 54%

The McMurry Coupling and Related Reactions

Ephritikhine

Villiers

2003

Modern Carbonyl Olefination

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Section: Intermolecular Cross-coupling Reactionsmentioning

confidence: 54%

The McMurry Coupling and Related Reactions

Ephritikhine

Villiers

2003

Modern Carbonyl Olefination

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“…In our previous study, the Prins/Conia-ene cascade cyclization of sterically hindered substrate (Scheme ) provided only modest yields even in high reaction temperature . Thus, the Prins/Conia-ene cascade cyclization between two sterically demanding substrates, β-keto ester 5 and alkynal 7 , was studied. Fortunately, our optimal condition (In(OTf) 3 /CH 3 CN) provided 80% yield of 1-oxadecalin 3 as a single diastereomer .…”

Section: Resultsmentioning

confidence: 99%

Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach

Huang

Lee

2011

J. Org. Chem.

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A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf)(3) in CH(3)CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.

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“…To a solution of 3b (2.195 g, 19.6 mmol) in 25 mL of CH 2 Cl 2 were added 3,4-dihydro-2 H -pyran (1.95 mL, 21.5 mmol) and p -TsOH (12 mg, 0.06 mmol). The reaction was stirred for 1.5 h, quenched with saturated NaHCO 3 (15 mL), extracted with CH 2 Cl 2 (3 × 30 mL), and the organic layers were combined and dried (MgSO 4 ).…”

Section: Methodsmentioning

confidence: 99%

The Intramolecular Allenolate Rauhut–Currier Reaction

et al. 2012

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An intramolecular Rauhut-Currier reaction utilizing alkynoates as the initial conjugate acceptor affords densely functionalized 5- and 6-membered rings from ynoate-enoate, ynoate-enenitrile, and alkynyl sulfone-enenitrile substrates. Trialkylphosphines catalyze the reaction, and TMSCN serves as a pronucelophile to effect turnover of the catalyst and the formation of a second C-C bond. Because of the highly electrophilic alkyne acceptor, this reaction yields products that cannot be easily accessed from the traditional Rauhut-Currier reaction.

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A McMurry Route to the Dienediyne Portion of Models of the Neocarzinostatin Chromophore

Cited by 12 publications

References 86 publications

The McMurry Coupling and Related Reactions

The McMurry Coupling and Related Reactions

Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach

The Intramolecular Allenolate Rauhut–Currier Reaction

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