Total Synthesis of Solandelactones A and B

Eichenauer, Nils C.; Nordschild, Anja C.M.; Bischop, Martina; Schumacher, Dominik; Mackwitz, Marcel K. W.; Tschersich, Roxanne; Wilhelm, Thorsten; Pietruszka, Jörg

doi:10.1002/ejoc.201500700

Cited by 18 publications

(8 citation statements)

References 58 publications

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“…The O -protected allylic alcohols (OAc, OBz, OBn, and OSiEt 3 , respectively) for the cross-metathesis were prepared following reported procedures …”

Section: Methodsmentioning

confidence: 99%

Exploitation of a Multienzymatic Stereoselective Cascade Process in the Synthesis of 2-Methyl-3-Substituted Tetrahydrofuran Precursors

et al. 2017

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Enantiopure 2-methyl-3-substituted tetrahydrofurans are key precursors of several biologically active products (drugs, flavors, and agrochemicals). Thus, a stereocontrolled and efficient methodology for the obtainment of these synthons is highly desirable. We exploited a two-step multienzymatic stereoselective cascade reduction of α-bromo-α,β-unsaturated ketones to give the corresponding bromohydrins in good yields, with high ee and de values. The cascade process is catalyzed by an ene-reductase and an alcohol dehydrogenase. Further manipulations of these bromohydrins, by two diastereodivergent routes, allowed the preparation of the tetrahydrofuran synthons. One route is based on a lipase catalyzed cleavage of the protecting group. The second route is characterized by a camphor sulfonic acid mediated isomerization of a β-hydroxyepoxide to give the tetrahydrofuran-2-ol. Finally, the synthesis of the most odorous and pleasant stereoisomer of the roasted meat aroma, i.e., (2S,3R)-2-methyl-3-thioacetate tetrahydrofuran, is reported as well.

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“…The O -protected allylic alcohols (OAc, OBz, OBn, and OSiEt 3 , respectively) for the cross-metathesis were prepared following reported procedures …”

Section: Methodsmentioning

confidence: 99%

Exploitation of a Multienzymatic Stereoselective Cascade Process in the Synthesis of 2-Methyl-3-Substituted Tetrahydrofuran Precursors

et al. 2017

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“…Horner-Wadsworth-Emmons reaction between aldehyde 32 25 and phosphonates 33a and 33b, which were respectively prepared from L-and D-serines in optically pure forms, afforded α,β-unsaturated ketones 34a and 34b (Scheme 9). This is the first branching point to deliver the C14 stereoisomers.…”

Section: Pietruszka's Synthesis Of Solandelactone I For the Structuramentioning

confidence: 99%

Recent topics of the stereodivergent synthesis of natural products

Takamura

2018

Tetrahedron Letters

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“…Except for the NLPHL-IA, all trials were registered at Current Controlled Trials (ISRCTN63474366, ISRCTN04761296, ISRCTN32443041) and recently published von Tresckow et al, 2012;Behringer et al, 2014). In NLPHL-IA, patients were treated with 30 Gy involved-field RT (IFRT) and followed up for tumour status and survival (Eichenauer 2015).…”

Section: Patientsmentioning

confidence: 99%

Impact of centralized diagnostic review on quality of initial staging in Hodgkin lymphoma: experience of the German Hodgkin Study Group

et al. 2015

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SummaryAccurate clinical staging is crucial for adequate risk-adapted treatment in Hodgkin lymphoma (HL) to prevent patients from under-or over-treatment. Within the latest German Hodgkin Study Group trial generation, diagnostic findings such as histopathology, computerized tomography imaging and clinical risk factors were re-evaluated by expert panels. Here, we retrospectively analysed 5965 patients and identified 399 in who major discordant findings changed their first-line treatment allocation. Histopathology review did not confirm the initial diagnosis of HL in 87 patients. Treatment allocation was revised in 312 of the remaining 5878 patients: 176 were assigned to a higher and 128 to a lower risk group, respectively; the correct treatment group remained unclear in 8 patients. Cases of revised treatment allocation accounted for 9Á8%, 6Á0%, 0Á8%, and 14Á8% of patients initially assigned to the HD13, HD14, HD15 trials and stage IA lymphocyte-predominant HL project, respectively. Most revisions were due to wrong application of clinical stage (20Á5% of 312 patients with revised treatment group), histological subtype (9Á0%) or the risk factors ≥3 involved areas (46Á8%) or large mediastinal mass (9Á3%). In conclusion, centralized review by experienced experts changed risk-adapted first-line treatment in a relevant proportion of HL patients. Quality control measures clearly improve the accuracy of treatment and should be implemented in clinical practice.

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Total Synthesis of Solandelactones A and B

Cited by 18 publications

References 58 publications

Exploitation of a Multienzymatic Stereoselective Cascade Process in the Synthesis of 2-Methyl-3-Substituted Tetrahydrofuran Precursors

Exploitation of a Multienzymatic Stereoselective Cascade Process in the Synthesis of 2-Methyl-3-Substituted Tetrahydrofuran Precursors

Recent topics of the stereodivergent synthesis of natural products

Impact of centralized diagnostic review on quality of initial staging in Hodgkin lymphoma: experience of the German Hodgkin Study Group

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