Furanosteroid studies. Improved synthesis of the A,B,C,E-ring core of viridin

Mascall, Kristen C.; Jacobi, Peter A.

doi:10.1016/j.tetlet.2012.01.070

Cited by 11 publications

(6 citation statements)

References 24 publications

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“…Another core framework of many natural products is the furan-fused cycloalkanone such as radermachol, [74][75][76][77][78] bhimamycin B, [71,72] halenaquinone, [64,65] and viridin [79][80][81][82] Mixture of furandicarbaldehyde 84.1 & glyoxal 84.2 in the presence of potassium cyanide give 84.3 (yields 66 %), which on reductive acylation gives 84, a polysubstituted IBF (Scheme 58). [187,188] Though there were several method available for the preparation of furo[3,4-c]quinolone 85, but the reduction technique utlizing hydrogen and palladium charcoal was a fascinating one.…”

Section: Mn Catalystmentioning

confidence: 99%

“…Another core framework of many natural products is the furan‐fused cycloalkanone such as radermachol, [74–78] bhimamycin B, [71,72] halenaquinone, [64,65] and viridin [79–82] which has great importance in pharmaceutical industry. As above mentioned radermachol contains a unique cycloheptanone‐ b,c ‐fused furan, the main potential component of folk medicine.…”

Section: Synthetic Routes Toward Fused Furanmentioning

confidence: 99%

“…Hibiscone C 12, [73] a sesquiterpene furanosteroid consists of both b and c-fused furan. Radermachol [74][75][76][77][78] and viridin [79][80][81][82] both have huge importance in pharmaceutical chemistry. Another interesting building scaffold is Granaticin A's core consisting of 3,4-fused furan.…”

Section: Introductionmentioning

confidence: 99%

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A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Manna¹,

Giri

Mondal³

et al. 2023

ChemistrySelect

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c‐fused furan and their derivatives are widely used as essential components of agrochemicals, bioregulators, dyes, essential skin and hair oils, cosmetics, flavouring agents, photosensitizers in industry and also show a broad range of biological activity. To the best of our knowledge, as of yet, no review has been published that covers the entire synthetic pathway leading to the formation of just c‐fused or 3, 4‐fused furans. In this review, we outline the various pathways for bicyclic, tricyclic, and polycyclic c‐fused furans, along with their detailed mechanisms, concrete examples, and biological activity. We have focused particularly on the synthetic route to medicine, natural products, and their analogues, such as c‐fused furanoditerpenes isospongiadiol, radermachol, a potential folk medicine ingredient, furo[3,4]quinolin‐4(5H)‐ones core, an inhibitor of lymphoma, bhimamycin B, hibiscone‐c core moiety of antibiotic lactonamycin, and analogue of natural product furanether A/ furanether B. Previous approaches and recent methods are described including metal‐free, transition metal, bio‐catalyst, and multi‐substrate approaches with mechanisms. The review covers the literature for more than six decades and presents an overview of the synthesis of different c‐fused furans and their utility in various disciplines such as synthetic chemistry, medicinal chemistry, and drug discovery.

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Section: Mn Catalystmentioning

confidence: 99%

Section: Synthetic Routes Toward Fused Furanmentioning

confidence: 99%

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A Detailed Review on C‐Fused Furan/3,4‐Fused Furan Analog and its Potential Applications

Manna¹,

Giri

Mondal³

et al. 2023

ChemistrySelect

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“…26 There are also several incomplete syntheses targeting either the core or some select rings. 27−29 Five years ago, 30,31 and more recently, 32 our group completed the synthesis of the A,B,C,E-ring core of viridin and wortmannin. The skeleton contained many of the key structural features found in 1 and 2, but lacked the D ring and also the C2-and C3-functional groups.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In the case of wortmannin, Shibasaki has accomplished two racemic and one formal enantioselective syntheses. − Only one total synthesis of viridin in racemic form has been achieved, by the Sorensen group . There are also several incomplete syntheses targeting either the core or some select rings. − Five years ago, , and more recently, our group completed the synthesis of the A,B,C,E-ring core of viridin and wortmannin. The skeleton contained many of the key structural features found in 1 and 2 , but lacked the D ring and also the C2- and C3- functional groups.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Studies on Furanosteroids: Construction of the Viridin Core Structure via Diels–Alder/retro-Diels–Alder and Vinylogous Mukaiyama Aldol-Type Reaction

Onyango

Jacobi

2012

J. Org. Chem.

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The synthesis of the viridin class of furanosteroids core skeleton from the readily available 2,3-dihydro-4-hydroxyinden-1-one (6) is described. Our strategy was broken down into three parts: (1) Synthesis of functionalized alkyne oxazoles of type 5; (2) intramolecular Diels-Alder/retro-Diels-Alder reaction of 5 followed by tautomerization and elaboration of R to give silylated furanonaphthols 4 bearing an aldehyde side chain; and (3) annulation of ring A by intramolecular vinylogous Mukaiyama aldol-type cyclization. Two major challenges were faced in the last step: (i) furanonaphthol derivatives bearing a β-hydroxyaldehyde functionality (R(1) = OH) suffered from dehydration to the E-enal, which is geometrically incapable of cyclization, and (ii) the functionality at C17 had a strong influence on the conversion of 4 to 3, as exemplified by the failure of the free ketone (X = O) or its derivatives (X = H, OH; X = H, OAc) to cyclize. In the end, success was realized with the analogous C17-norketone (X = H, H).

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