4.8 Article

A Convergent Total Synthesis of (±)-γ-Rubromycin

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 16, 页码 6114-6117

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AMER CHEMICAL SOC
DOI: 10.1021/ja1115524

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资金

  1. National Science Foundation [0135031, 0806356]
  2. University of California Tobacco
  3. ACS Division of Organic Chemistry (SURF)
  4. Pfizer-La Jolla
  5. UCSB
  6. Direct For Mathematical & Physical Scien [0806356, 0135031] Funding Source: National Science Foundation
  7. Division Of Chemistry [0806356, 0135031] Funding Source: National Science Foundation

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An expeditious convergent total synthesis affords (+/-)-gamma-rubromycin (1) in 4.4% overall yield. The longest linear sequence is 12 steps from commercial starting materials. The effort highlights a remarkable late-stage oxidative [3 + 2] cycloaddition for construction of the spiroketal, a regioselective carbonyl methylenation, a boron tribromide promoted deprotection, ortho- to para-naphthoquinone spiroketal rearrangement, and a tautomerization sequence.

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