Convergent synthesis of (+)-muconin

Yang, Wenqian; Kitahara, Takeshi

doi:10.1016/s0040-4039(99)01629-9

Cited by 27 publications

(6 citation statements)

References 15 publications

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“…[12] Next, we examined the selective reduction of enediyne 17 by using catalytic [13] or stoichiometric [14] amounts of Wilkinson catalyst, but compound 18 was obtained in moderate yields (Scheme 5). Marshall and Chen employed diimide instead of the Wilkinson catalyst for the selective reduction of an enyne.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity

Maezaki

Tominaga

Kojima

et al. 2005

Chemistry A European J

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Convergent total syntheses of murisolin (1), natural 16,19-cis-murisolin 2, and unnatural 16,19-cis-murisolin 3 were accomplished by asymmetric alkynylation of alpha-tetrahydrofuranic aldehyde with a diyne and Sonogashira coupling with a gamma-lactone segment as the key steps. Stereoisomers of alpha-tetrahydrofuranic aldehyde were synthesized with high optical purity and the asymmetric alkynylation of these with 1,6-heptadiyne proceeded in good yield and with high diastereoselectivity. The cell-growth inhibition profile and COMPARE analysis of the synthetic compounds 1-3 were also investigated.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Murisolins and Evaluation of Tumor‐Growth Inhibitory Activity

Maezaki

Tominaga

Kojima

et al. 2005

Chemistry A European J

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“…(+)-Muconin ( 1 ) showed a potent cytotoxicity against human pancreatic and breast tumor cells . Because of its interesting biological activities and its unique structure, synthetic studies of (+)-muconin were undertaken by some groups. − To synthesize (+)-muconin ( 1 ), formation of the THF-THP core part in a stereoselective manner is an important step. In terms of the THP ring formation, our group accomplished synthesis of pyranicin and decytospolide A and B, which possess cis -2,6-disubstituted THP rings, using diastereoselective oxypalladation. − There are several examples of syntheses of THP-containing natural products using oxypalladation. − Herein, we wish to report the construction of THF-THP rings using diastereoselective oxypalladation and its application to the total synthesis of (+)-muconin ( 1 ).…”

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confidence: 99%

Synthesis of (+)-Muconin via Diastereoselective Oxypalladation

et al. 2021

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Synthesis of (+)-muconin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran (THF-THP) ring moiety was performed using diastereoselective oxypalladation in the presence of CuCl2. The cross-coupling reaction of the THF-THP moiety with the γ-lactone portion followed by reduction of the enyne and removal of the protecting groups afforded (+)-muconin.

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“…The ketone derivative (7) showed apparently decreased activity, indicating that the hydroxyl groups adjacent to the THP ring play a critical role for cytotoxic activity. The fact that the hydroxyl-protected analogs (9,10,11,12) exhibited the lowest potency also proves that the number of hydroxyl groups is an important factor. The saturated lactone compound (8) having almost the same activity as muconin, is about 5-fold more potent than the unsaturated counterpart (7).…”

Section: Introductionmentioning

confidence: 91%