Total Synthesis of (−)-Rhodomollanol A

Gao, Jianhong; Rao, P.V.D. Somasekhar; Xu, Kaixiang; Wang, Shuaifeng; Wu, Yi; He, Chi; Ding, Hanfeng

doi:10.1021/jacs.0c00308

Cited by 73 publications

(38 citation statements)

References 55 publications

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“…[25b,26] Reacting p-cresol 35 with MOMCl furnished compound 36 b. [27] For the preparation of tert-butyl ether 36 c a methold of Livinghouse et al was adapted. [28] We also prepared the corresponding silyl ethers (SiMe 3 , SiMe 2 tBu) but they were not suitable for the organocuprate reaction.…”

Section: Resultsmentioning

confidence: 99%

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Approach to the Core Structure of Schweinfurthin B

Roos

Maier

2020

ChemistrySelect

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We investigated approaches to the xanthene part of schweinfurthin B. Starting from an exo‐methylene cyclohexanone, an organocuprate addition led to a cyclohexanone featuring a functionalized benzyl substituent in the 2‐position. Ring‐closing reactions to the tetrahydroxanthene core (formation of the central ring) were possible in moderate yield by attack of a phenolic oxygen function on the keto group. More effective was the cyclization to the xanthene core structure after conversion of the cyclohexanone to the exo‐methylene cyclohexane derivative and Lewis acid mediated addition of the phenolic OH to the double bond. In addition, we tried to form the xanthene ring system in a model study by cycloaddition reaction of a silyl enol ether with an ortho‐quinone methide.

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Section: Resultsmentioning

confidence: 99%

“…To obtain dimethoxy derivative 36 a , phenol 35 was reacted with methyl iodide in presence of K 2 CO 3 using acetonitrile as solvent [25b,26] . Reacting p ‐cresol 35 with MOMCl furnished compound 36 b [27] . For the preparation of tert ‐butyl ether 36 c a methold of Livinghouse et al.…”

Section: Resultsmentioning

confidence: 99%

Approach to the Core Structure of Schweinfurthin B

Roos

Maier

2020

ChemistrySelect

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“…31 Ding and co-workers also used this strategy in a recent synthesis of (-)-rhodomollanol A (not shown). 32 Jorumycin Although one of the earliest known dearomative methods, the hydrogenation of arenes and heteroarenes remains a vibrant and active field of research to this day. Advances in enantioselective catalysis as well as functional-group and heterocyclic tolerance have established dearomative hydrogenation as one of the premier methods for generating complex, saturated cyclic structures.…”

Section: Isocarbostyril Alkaloidsmentioning

confidence: 99%

Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization

Huck

Šarlah

2020

Chem

170

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Dearomatization is a fundamental chemical transformation, and it underlies some of the most efficient tactics for generating threedimensional complexity from basic two-dimensional precursors. The dearomative toolbox, once restricted to only a handful of reactions, has begun to grow more sophisticated as novel methods are added, introducing more functionality under milder conditions and with more control over chemo-, regio-, and stereoselectivity than ever before. Over the past two decades, major developments in dearomative processes have bolstered significant total-synthesis endeavors and greatly expanded the scope and complexity of chemical building blocks accessible from feedstock arenes. In this Perspective, we highlight some of the recent advances and key challenges that remain in this vibrant area of organic chemistry.

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“…The Ding group disclosed an unprecedented Lewis acid mediated retro-Dieckmann fragmentation/vinylogous Dieckmann cyclization cascade of tetracyclic ketone 156 to enone 157 for the installation of a bicyclo[3.3.0]octane unit in a total synthesis of the diterpenoid (-)-rhodomollanol A (158; Scheme 44). 109…”

Section: Account Synlettmentioning

confidence: 99%

Adventures and Detours in the Synthesis of Hydropentalenes

Deimling

Zens

Park

et al. 2020

Synlett

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Functionalized hydropentalenes (i.e., bicyclo[3.3.0]octanones) constitute important building blocks for natural products and for ligands for asymmetric catalysis. The assembly and tailored functionalization of this convex roof-shaped scaffold is challenging and has motivated a variety of synthetic approaches including our own contributions, which will be presented in this account.1 Introduction2 Biosynthesis of Hydropentalenes3 Hydropentalenes through the Pauson–Khand Reaction4 Hydropentalenes through Transannular Oxidative Cyclization of Cycloocta-1,4-diene5 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Dodecahydrocyclopenta[a]indenes6 Functionalization of Bicyclo[3.3.0]octan-1,4-diones to Crown Ether Hybrids7 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Cylindramide8 Tandem Ring-Opening Metathesis/Ring-Closing Metathesis/Cross-Metathesis of Bicyclo[2.2.1]heptanes9 Functionalization of Bicyclo[3.3.0]octan-1,4-dione to Geodin A10 Hydropentalenes through Enantioselective Desymmetrization of Weiss Diketones11 Functionalization of Weiss Diketones by Carbonyl Ene Reactions12 Functionalization of the Weiss Diketone to Cylindramide and Geodin A Core Units13 Biological Properties of Bicyclo[3.3.0]octanes14 Hydropentalenes through Vinylcyclopropane Cyclopentene Rearrangement15 Functionalization of Bicyclo[3.3.0]octanes toward Chiral Dienes16 Miscellaneous Syntheses of Hydropentalenes17 Conclusion and Outlook

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Total Synthesis of (−)-Rhodomollanol A

Cited by 73 publications

References 55 publications

Approach to the Core Structure of Schweinfurthin B

Approach to the Core Structure of Schweinfurthin B

Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization

Adventures and Detours in the Synthesis of Hydropentalenes

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