An "Inside-Out" Strategy Enables a 14-Step Total Synthesis of Hispidospermidin.

Charis Amber, Tenta Nakamura, Matthew Amoako, Nicholas S Settineri, Richmond Sarpong

Abstract read

In one paragraph

Article in JACS Au, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

5 authors.

Charis AmberDepartment of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.ORCID https://orcid.org/0000-0002-3671-5388

Tenta NakamuraDepartment of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.ORCID https://orcid.org/0009-0003-2406-2927

Matthew AmoakoDepartment of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.

Nicholas S SettineriDepartment of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.ORCID https://orcid.org/0000-0003-0272-454X

Richmond SarpongDepartment of Chemistry, University of California, Berkeley, Berkeley, California 94720, United States.ORCID https://orcid.org/0000-0002-0028-6323

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026

$5.4M

NIGMS NIH HHS R35 GM130345

6 · The paper itself

Abstract

Traditionally, a retrosynthesis aims to disconnect a molecular target into simpler precursors as quickly as possible, prioritizing the early deconstruction of primary contributors to the molecule's overall structural complexity (i.e., primary complexity elements). The complementary approach, which rapidly constructs complexity early in the forward synthesis, is much less common. Herein, we report a 14-step protective group-free total synthesis of the polycyclic sesquiterpenoid alkaloid hispidospermidin, which exploits an early-stage complexity-generating bicycle formation to forge the carbon skeleton, followed by subsequent peripheral functionalizations. Specifically, a key Giese conjugate addition of a bridgehead radical established the quaternary center, and a novel isomerization was discovered, which enabled a one-pot protocol to establish the

Indexed as

hispidospermidininside-out strategyisomerizationretrosynthesistotal synthesis

Identifiers

PMID41614197

DOI10.1021/jacsau.5c01567

PMCPMC12848721

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LicenceCC BY-NC-ND

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.