On the diastereocontrol in the formation of (2R,3S)-3-(3′-furyl)-1,2-O-isopropylidenedioxy-3-pentanol and its (2R,3R)-diastereomer

Hui, Chi Wai; Lee, Hing Ken; Wong, H. N. C.

doi:10.1016/s0040-4039(01)02055-x

Cited by 16 publications

(3 citation statements)

References 15 publications

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“…3-Lithiofurans have been used as nucleophiles, as can be seen in recently reported additions to aldehydes, as in the synthesis of the tetracyclic decalin part of azadirachtin 56 and cyclic terpenoids, or to ketones, as in the reaction between 3-furyllithium ( 24 ) and the chiral pentanone 23 in studies toward the synthesis of marine natural products plakortones. The reaction shows a high dependence of the solvent, toluene affording the anti -diastereomer 25 as the major one (Scheme ), whereas when the addition is performed in diethyl ether the syn -isomer is predominantly obtained . Moreover, addition to lactones 51 and (η 3 -dihydropyridyl)molybdenum complexes 60 and formylation reactions have also been reported …”

Section: 11 Aromatic Five-membered Ringsmentioning

confidence: 97%

Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry

2004

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Section: 11 Aromatic Five-membered Ringsmentioning

confidence: 97%

Metalated Heterocycles and Their Applications in Synthetic Organic Chemistry

2004

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“…A somewhat lengthy synthesis of (À )-plakortone B (122) with early stage furofuranone construction from D-mannitol has been reported by Wong and co-workers (Scheme 25). [57] Dmannitol derived 171 [58] was converted to TMS-furan 173 via αsilylation and protecting group interchange. Compound 173 via sequential double oxidation-Grignard addition followed by peracetic acid oxidation furnished butenolide 175 via the ketone 174.…”

Section: Wong Synthesis Of (à )-Plakortone B (122)mentioning

confidence: 99%

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

et al. 2020

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The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

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“…Thus, it is evident that the size of the protecting group played a major role in controlling the stereochemistry of the carbon carrying the tertiary hydroxyl group during the Grignard reaction. More systematic studies are needed to elucidate the origin of the distinct different stereochemical outcome of vinylmagnesium bromide addition to the carbonyl group of α‘,α,β-trioxygenated ketones ( 7 , 13a − c ), since several chelated as well as nonchelated transition states are feasible …”

mentioning

confidence: 99%