Stereoselective synthesis of demethylgorgosterol

Ishiguro, Masaji; Akaiwa, Akira; Fujimoto, Yoshinori; Sato, Susumu; Ikekawa, Nobuo

doi:10.1016/s0040-4039(01)86033-0

Cited by 9 publications

(2 citation statements)

References 11 publications

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“…The aldehyde 25 was very similar to the known aldehyde 12 used by Ikekawa et al. in their semisynthesis, the only difference being the protecting group for the A/B‐ring [18b] . Therefore, the same procedures were used to synthesize the ketone 8 from the aldehyde 25 .…”

Section: Resultsmentioning

confidence: 92%

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

et al. 2021

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In this study, we report a convenient and high yielding formal semisynthesis of demethylgorgosterol, a marine steroid with an intriguing sidechain containing a cyclopropane unit. This was achieved through the synthesis of an advanced ketone intermediate. The synthetic route features a total of ten steps, starting from commercially available stigmasterol, with an overall yield of 27 %. The key step was a stereoselective intermolecular cyclopropanation reaction. This reaction proceeded in 82 % yield, the resulting cyclopropane carboxylic ester shows a trans/cis ratio of 89 : 11, with a diastereomeric ratio for the trans‐diastereomers of >99 : 1. A reduction/oxidation sequence afforded the corresponding aldehyde, which was used in a Grignard reaction. A final oxidation step then yielded the desired ketone. This novel route presents a platform to further investigate the medicinal applications of gorgosterol‐type steroids and to fully understand their role in coral symbiosis.

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Section: Resultsmentioning

confidence: 92%

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

et al. 2021

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“…(3 H, d,J = 6.73 Hz, 21-CH3), 0.861 (3 H, d, J = 6.55 Hz, 26-CH3), 0.868 (3 H, d, J -6.56 Hz, 27-CH3), 9.75 (1 H, br s, 29-CH). Both 15a and 15b had the same mass spectrum, m/z (relative intensity) 428 (M+, 18), 410 (14), 395 (11), 384 (25), 343 (14), 325 (7), 317 (9), 316 ( 9), 300 ( 14), 299 (42), 271 (42), 255 (38), 246 (22), 231 (53), 229 (40), 213 (100).…”

Section: Methodsmentioning

confidence: 99%

Stereoselective synthesis of (22R)- and (22S)-22-methylcholesterol

Zielinski¹,

Li²,

Djerassi³

1982

J. Org. Chem.

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Dinophyceae (Dinoflagellates)

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: General Aspects Classification of Dinoflagellates Photosynthetic Pigments Sulfated Exopolysaccharides Sterols Fatty Acids Glycolipids Amphidinols and other Polyhydroxylated Polyenic Derivatives Toxic Proliferations: Endotoxins and Exotoxins Main Types of Dinoflagellate Toxins Cyclic Polyethers Okadaic Acid and Derivatives Toxic Macrolides: Amphidinolides, Caribenolide, Goniodomin A , Hoffmanniolide Complexity of the Biosynthesis of Polyketides Saxitoxin and its Derivatives Nitrogenous Toxins with Imine Function Zooxanthellatoxins ( ZTs ) and other Nitrogenous Toxins Pfiesteria piscicida : A Particularly Toxic Dinoflagellate Sulfur‐Containing Derivatives Phosphorus Derivatives and other Unusual Compounds

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Stereoselective synthesis of demethylgorgosterol

Cited by 9 publications

References 11 publications

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

Stereoselective synthesis of (22R)- and (22S)-22-methylcholesterol

Dinophyceae (Dinoflagellates)

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