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Search for "oxazololomycin" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Progress in the total synthesis of inthomycins

Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

application of various efforts towards the synthesis of inthomycins and their analogues systematically. Keywords: antibiotics; inthomycins; oxazololomycin; Stille coupling; total synthesis; Introduction Inthomycins, alternatively known as phthoxazolins, are a class of compounds in which a methylene

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Graphical Abstract

Figure 1: The inthomycins A–C (1–3) and structurally closely related compounds.

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Figure 2: Syntheses of inthomycins A–C (1–3).

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Scheme 1: The first total synthesis of racemic inthomycin A (rac)-1 by Whiting.

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Scheme 2: Moloney’s synthesis of the phenyl analogue of inthomycin C ((rac)-3).

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Scheme 3: Moloney’s synthesis of phenyl analogues of inthomycins A (rac-1) and B (rac-2).

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Scheme 4: The first total synthesis of inthomycin B (+)-2 by R. J. K. Taylor.

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Scheme 5: R. J. K. Taylor’s total synthesis of racemic inthomycin A (rac)-1.

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Scheme 6: The first total synthesis of inthomycin C ((+)-3) by R. J. K. Taylor.

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Scheme 7: The first total synthesis of naturally occurring inthomycin C ((–)-3) by Ryu et al.

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Scheme 8: Preparation of E,E-iododiene (+)-84 and Z,E- iododiene 85a.

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Scheme 9: Hatakeyama’s total synthesis of inthomycin A (+)-1 and inthomycin B (+)-2.

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Scheme 10: Hatakeyama’s total synthesis of inthomycin C ((–)-3).

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Scheme 11: Maulide’s formal synthesis of racemic inthomycin C ((rac)-3).

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Scheme 12: Hale’s synthesis of dienylstannane (+)-69 and enyne (+)-82b intermediates.

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Scheme 13: Hale’s total synthesis of inthomycin C ((+)-3).

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Scheme 14: Hale and Hatakeyama’s resynthesis of (3R)-inthomycin C (−)-3 Mosher esters.

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Scheme 15: Reddy’s formal syntheses of inthomycin C (+)-3 and inthomycin C ((−)-3).

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Scheme 16: Synthesis of the cross-metathesis precursors (rac)-118 and 121.

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Scheme 17: Donohoe’s total synthesis of inthomycin C ((−)-3).

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Scheme 18: Synthesis of dienylboronic ester (E,E)-128.

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Scheme 19: Synthesis of the alkenyl iodides (Z)- and (E)-130.

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Scheme 20: Burton’s total synthesis of inthomycin B ((+)-2).

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Scheme 21: Burton’s total synthesis of inthomycin C ((−)-3).

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Scheme 22: Burton’s total synthesis of inthomycin A ((+)-1).

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Scheme 23: Synthesis of common intermediate (Z)-(+)-143a.

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Scheme 24: Synthesis of (Z)-and (E)-selective fragments (+)-145a–c.

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Scheme 25: Kim’s total synthesis of inthomycins A (+)-1 and B (+)-2.

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Scheme 26: Completion of total synthesis of inthomycin C ((–)-3) by Kim.

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Review

Published 07 Jan 2021

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