Formal Synthesis of (+)-Sorangicin A

Crimmins, Michael T.; Haley, Matthew W.; O'Bryan, Elizabeth A.

doi:10.1021/ol201920j

Cited by 33 publications

(14 citation statements)

References 34 publications

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“…3g Alcohol 20 was subjected further to Mitsunobu reaction 3b,7 in the presence of PTSH ( 21 ), di-isopropyl azo dicarboxylate (DIAD), and Ph 3 P to access sulfide 22 which finally was oxidized to sulfone 12 in 75% overall yield using(NH 4 ) 6 Mo 7 O 24 ·4H 2 O in the presence of 30% aqueous H 2 O 2 . 3b,8…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Cytospolide Q

2018

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A flexible and convergent strategy for the stereoselective total synthesis of bioactive marine natural product cytospolide Q has been developed. The key features of this synthesis include Evans anti-aldol reaction for the installation of C-2 and C-3 stereocenters and cycloetherification via epoxide opening followed by concomitant lactonization for the construction of tetrahydrofuran and γ-butyrolactone scaffolds. This synthetic study also revealed that protected oxygenated functionality (methyl ester or benzyl ether) at C-1 position participated readily in epoxide opening.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Cytospolide Q

2018

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“…Although effective, the first-generation synthesis of (−)- 5 was not considered sufficiently efficient vis-à-vis material advancement; a second generation approach based on precedence from the Crimmins laboratory 11a was therefore developed. Early on we had recognized that the pyran portion of bicyclic aldehyde (−)- 5 shares the same 2,6- trans -relationship as dihydropyran 7 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…al. 11 Herein we provide a full account on the evolution of a synthetic strategy, that in 2009 led to the first, and to date only, total synthesis of this architecturally intriguing antibiotic. 12 …”

Section: Introductionmentioning

confidence: 99%

(+)-Sorangicin A: evolution of a viable synthetic strategy

et al. 2011

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An effective, asymmetric total synthesis of the antibiotic (+)-sorangicin A (1) has been achieved. Central to this venture was the development of first and second generation syntheses of the signature dioxabicyclo[3.2.1]octane core, the first featuring chemo- and stereoselective epoxide ring openings facilitated by a Co2(CO)6-alkyne complex, the second involving a KHMDS-promoted epoxide ring formation/opening cascade. Additional highlights include effective construction of the dihydro- and tetrahydropyran ring systems, respectively via a stereoselective conjugate addition/α-oxygenation protocol and a thioketalization/hydrostannane reduction sequence. Late-stage achievements entailed two Julia–Kociénski olefinations to unite three advanced fragments with high E-stereoselectivity, followed by a modified Stille protocol to introduce the Z,Z,E trienoate moiety, thereby completing the carbon skeleton. Mukaiyama macrolactonization, followed by carefully orchestrated Lewis and protic acid-promoted deprotections that suppressed isomerization and/or destruction of the sensitive (Z,Z,E)-trienoate linkage completed the first, and to date only, total synthesis of (+)-sorangicin A (1)

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“…[13] Other chelate-controlled addition reactions have been used such as ZnMe 2 for the synthesis of (+)-sorangicin. [14] Moreover, in the syntheses of (+)-euphococcinine and (+)-adaline, [15] AlMe 3 was used as a Lewis acid and TiCl 2 (iPrO) 2 , Yb(OTf) 3 , and MgBr 2 ·(OEt) 2 were used as transmetalating agents, which were also useful in the syntheses of pestalotiopsin A, [16] phomactins [17] and salvinorin A. [18] Carboalumination addition reactions are not frequently employed.…”

Section: Introductionmentioning

confidence: 99%

Addition of Vinylmetallic Reagents to Chiral 2‐Formyltetrahydrofuran

Lamariano‐Merketegi¹,

Lorente²,

Gil³

et al. 2014

Eur J Org Chem

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Polyketide macrolides, which belong to an interesting family of metabolites, are complex structures with valuable bioactivity. In this work, several procedures for the bond formation between a vinylorganometallic reagent and a chiral formyl-THF compound were examined for the subsequent application to the total synthesis of phormidolides. Model molecules were synthesized to study and optimize the method that

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Formal Synthesis of (+)-Sorangicin A

Cited by 33 publications

References 34 publications

Total Synthesis of Cytospolide Q

Total Synthesis of Cytospolide Q

(+)-Sorangicin A: evolution of a viable synthetic strategy

Addition of Vinylmetallic Reagents to Chiral 2‐Formyltetrahydrofuran

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